Conditions | Yield |
---|---|
With lithium; ferric nitrate In ammonia at -50℃; for 2h; | 95% |
With lithium amide In ammonia | 78% |
Multistep reaction; | |
Stage #1: methyl iodide With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 25℃; for 0.166667h; Inert atmosphere; Stage #2: propargyl alcohol at 25℃; for 10h; Inert atmosphere; |
2-(but-2-ynyloxy)-tetrahydro-2H-pyran
methyl propargyl alcohol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol | 95% |
With toluene-4-sulfonic acid In methanol | 59% |
3-chloro-2-buten-1-ol
methyl propargyl alcohol
Conditions | Yield |
---|---|
With sodium hydroxide In cyclohexane; water at 65 - 72℃; for 8h; | 88.1% |
With potassium hydroxide; tetra-(n-butyl)ammonium iodide In hexane for 12h; Heating; | 50% |
With ammonia; sodium; ferric nitrate for 14h; | 47% |
With ammonia; sodium amide Behandeln des Reaktions-Loesung mit NH4Cl; | |
With ammonia; sodium amide |
dilithium salt of propargyl alcohol
methyl iodide
methyl propargyl alcohol
Conditions | Yield |
---|---|
85% |
1-(methoxymethoxy)but-2-yne
methyl propargyl alcohol
Conditions | Yield |
---|---|
With bismuth(III) chloride; water In acetonitrile at 50℃; for 3h; | 85% |
(but-2-yn-1-yloxy)(tert-butyl)dimethylsilane
methyl propargyl alcohol
Conditions | Yield |
---|---|
With P(MeNCH2CH2)3N In dimethyl sulfoxide at 80℃; for 36h; desilylation; | 83% |
formaldehyd
1,2-propanediene
1-chloro-3,7-dimethylocta-2,6-diene
A
methyl propargyl alcohol
B
(6E)-7,11-dimethyldodeca-6,10-dien-2-yn-1-ol
Conditions | Yield |
---|---|
Stage #1: 1,2-propanediene With n-butyllithium In diethyl ether; hexane at -78 - -15℃; for 1.75h; Inert atmosphere; Stage #2: 1-chloro-3,7-dimethylocta-2,6-diene In diethyl ether; hexane at -15℃; for 5.05h; Inert atmosphere; Stage #3: formaldehyd Further stages; | A n/a B 68% |
formaldehyd
1-propynylmagnesium bromide
methyl propargyl alcohol
Conditions | Yield |
---|---|
With diethyl ether |
(Z)-3-chloro-2-but-en-1-ol
methyl propargyl alcohol
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide | |
With sodium hydroxide |
Conditions | Yield |
---|---|
With ammonia; sodium amide |
Conditions | Yield |
---|---|
With sodium |
Conditions | Yield |
---|---|
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; hexane at 0 - 50℃; for 4h; Inert atmosphere; | |
With n-butyllithium In tetrahydrofuran at -78℃; | |
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: formaldehyd In tetrahydrofuran at -78℃; | |
With copper(I) formate; water; calcium carbonate at 100℃; under 7600 Torr; |
Conditions | Yield |
---|---|
In diethyl ether |
Conditions | Yield |
---|---|
(i) aq. oxalic acid, (ii) Zn, AcOH, CuSO4; Multistep reaction; |
Conditions | Yield |
---|---|
With water at 25℃; Rate constant; pH 10-11; |
3-hydroxy-5-methyl-1H-pyrazole
A
trans-Crotonaldehyde
B
methyl propargyl alcohol
C
cis-crotonaldehyde
Conditions | Yield |
---|---|
at 600℃; Product distribution; Mechanism; various pyrazolines; |
Conditions | Yield |
---|---|
at 100℃; under 7355.08 Torr; |
methyl propargyl alcohol
Conditions | Yield |
---|---|
With diethyl ether; polyoxymethylene nachfolgendem Zersetzen des Reaktionsprodukts mit Eis und Salzsaeure; |
methyl propargyl alcohol
but-2-ynal
oxalic acid
acetic acid
A
meso-octa-2,6-diyne-4,5-diol
racem.-octa-2,6-diyne-4,5-diol
C
methyl propargyl alcohol
Conditions | Yield |
---|---|
at -10℃; |
Conditions | Yield |
---|---|
Stage #1: 1,1-dibromopropene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; |
methyl propargyl alcohol
Conditions | Yield |
---|---|
With N,N,N,N-tetraethylammonium tetrafluoroborate In methanol Electrochemical reaction; | 77 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: ethyl bromide With bromine; magnesium In tetrahydrofuran at 40℃; for 3h; Large scale; Stage #2: prop-1-yne In tetrahydrofuran at 15℃; for 12h; Large scale; Stage #3: With formaldehyd In tetrahydrofuran at 35 - 65℃; Temperature; Large scale; | 160 kg |
formaldehyd
carbon tetrabromide
acetaldehyde
methyl propargyl alcohol
Conditions | Yield |
---|---|
Stage #1: carbon tetrabromide; acetaldehyde With triphenylphosphine In dichloromethane at 0℃; Corey-Fuchs Alkyne Synthesis; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran at -78℃; Corey-Fuchs Alkyne Synthesis; Inert atmosphere; Stage #3: formaldehyd In tetrahydrofuran at -78 - 20℃; Corey-Fuchs Alkyne Synthesis; Inert atmosphere; |
Conditions | Yield |
---|---|
With bromine; triphenylphosphine In dichloromethane at 0℃; for 1h; | 100% |
With phosphorus tribromide | 89% |
With bromine; triphenylphosphine In dichloromethane at 0℃; for 1h; | 89% |
methyl propargyl alcohol
3-iodo-but-2-ene-1-ol
Conditions | Yield |
---|---|
Stage #1: methyl propargyl alcohol With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether; toluene at 0 - 23℃; Inert atmosphere; Stage #2: With iodine; ethyl acetate In diethyl ether; toluene at 0 - 23℃; Inert atmosphere; Darkness; | 100% |
Stage #1: methyl propargyl alcohol With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether; toluene at -78 - 20℃; for 12.5h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; diethyl ether; toluene at -78 - 20℃; Inert atmosphere; | 98% |
Stage #1: methyl propargyl alcohol With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether; ethyl acetate; toluene at 0 - 20℃; for 18.5h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; diethyl ether; ethyl acetate; toluene at -78 - 20℃; for 2h; | 94% |
methyl propargyl alcohol
dimethylsilicon dichloride
But-2-ynyloxy-chloro-dimethyl-silane
Conditions | Yield |
---|---|
Ambient temperature; | 100% |
methyl propargyl alcohol
N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide
N-tert-butoxycarbonyl-N-(but-2-yn-1-yl)-(4-methylphenyl)sulfonamide
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; Inert atmosphere; | 100% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 1h; Mitsunobu reaction; | 95% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Condensation; | 78% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 9h; |
methyl propargyl alcohol
4,6-dichloropyrimidine-5-carboxylic acid chloride
Conditions | Yield |
---|---|
With triethylamine at 0 - 20℃; | 100% |
methyl propargyl alcohol
3-iodo-2-buten-1-ol
Conditions | Yield |
---|---|
Stage #1: methyl propargyl alcohol With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran Stage #2: With iodine In tetrahydrofuran | 100% |
Stage #1: methyl propargyl alcohol With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether at 0 - 20℃; for 4h; Inert atmosphere; Stage #2: With iodine In diethyl ether at 0 - 20℃; for 8h; Inert atmosphere; | 99% |
Stage #1: methyl propargyl alcohol With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether; ethyl acetate; toluene at 0 - 20℃; for 18.5h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; diethyl ether; ethyl acetate; toluene at -78 - 20℃; for 2h; Inert atmosphere; | 78% |
Stage #1: methyl propargyl alcohol With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether at 0℃; for 1h; Stage #2: With iodine In diethyl ether at -78 - 20℃; for 1h; |
methyl propargyl alcohol
N-phenyl-benzimidoyl chloride
but-2-ynyl-N-phenylbenzimidate
Conditions | Yield |
---|---|
Stage #1: methyl propargyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 30℃; for 1.25h; Stage #2: N-phenyl-benzimidoyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h; | 100% |
methyl propargyl alcohol
tert-butylchlorodiphenylsilane
4-(tert-butyldiphenylsilyloxy)-1-butyne
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 2.5h; Sealed tube; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760.051 Torr; | 99% |
With hydrogen; Lindlar's catalyst | 95% |
With hydrogen In methanol at 20℃; under 760.051 Torr; for 5.5h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics; | A 99% B n/a |
methyl propargyl alcohol
N-(2-iodophenyl)methanesulfonamide
N-(but-2-yn-1-yl)-N-(2-iodophenyl)methanesulfonamide
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 3h; | 99% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 23h; | 99% |
methyl propargyl alcohol
(S)-4-methyl-N-(2-oxotetrahydrofuran-3-yl)benzenesulfonamide
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 10h; Mitsunobu reaction; Inert atmosphere; | 99% |
methyl propargyl alcohol
propynoic acid methyl ester
(E)-methyl 3-(but-2-ynyloxy)acrylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Inert atmosphere; | 99% |
methyl propargyl alcohol
bis(tri-n-butyltin)
(2E)-3-methyl-3-tributylstannylprop-2-en-1-ol
Conditions | Yield |
---|---|
Stage #1: bis(tri-n-butyltin) With n-butyllithium; copper(l) cyanide In tetrahydrofuran; hexane at -78 - -40℃; for 0.583333h; Inert atmosphere; Stage #2: methyl propargyl alcohol In tetrahydrofuran; methanol; hexane at -78 - -10℃; Inert atmosphere; | 99% |
With n-butyllithium; copper(l) cyanide In tetrahydrofuran; methanol at -78 - 20℃; | 99% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); oxygen In benzene-d6 at 80℃; for 1h; Reagent/catalyst; diastereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 0.5h; Mitsunobu Displacement; Inert atmosphere; | 99% |
methyl propargyl alcohol
3-phenyl-2H-1,4-benzoxazine
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In acetonitrile at 100℃; for 4h; Schlenk technique; Inert atmosphere; | 99% |
methyl propargyl alcohol
bis(tri-n-butyltin)
3-(tributylstannyl)but-2-en-1-ol
Conditions | Yield |
---|---|
With n-butyllithium; copper(l) cyanide In tetrahydrofuran at -10℃; Inert atmosphere; regioselective reaction; | 99% |
3,4-dihydro-2H-pyran
methyl propargyl alcohol
2-(but-2-ynyloxy)-tetrahydro-2H-pyran
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In diethyl ether 0 deg C, 0.5 h; 25 deg C, 1 h; | 98% |
With lanthanum(III) chloride In dichloromethane for 4h; Ambient temperature; | 93% |
With toluene-4-sulfonic acid at 0℃; for 3h; | 89% |
methyl propargyl alcohol
Tosyl isocyanate
but-2-yn-1-yl tosylcarbamate
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 20℃; for 2.5h; | 98% |
copper(l) iodide; triethylamine In tetrahydrofuran at 25℃; | |
With triethylamine In diethyl ether for 2h; Ambient temperature; Yield given; |
methyl propargyl alcohol
Conditions | Yield |
---|---|
With disulfur dichloride; triethylamine In diethyl ether at 0℃; for 1h; | 98% |
With disulfur dichloride; triethylamine In diethyl ether |
Conditions | Yield |
---|---|
With 1,2-bis-(diphenylphosphino)ethane; bis(1,5-cyclooctadiene)diiridium(I) dichloride In tetrahydrofuran for 2h; Heating; | 98% |
With zinc; CoI2(dppe) In tetrahydrofuran; acetonitrile at 80℃; for 12h; | 85% |
methyl propargyl alcohol
2-Mercaptobenzothiazole
2-but-2-ynylmercapto-benzothiazole
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; Mitsunobu substitution; | 98% |
Stage #1: methyl propargyl alcohol With 1H-imidazole; iodine; triphenylphosphine In dichloromethane for 0.75h; Inert atmosphere; Reflux; Stage #2: 2-Mercaptobenzothiazole In dichloromethane at 20℃; for 2h; Inert atmosphere; | 53% |
methyl propargyl alcohol
N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide
tert-butyl but-2-yn-1-yl[(2-nitrophenyl)sulfonyl]carbamate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 22h; Mitsunobu reaction; | 98% |
methyl propargyl alcohol
dimethyl deca-2,8-diynedioate
4-methyl-1-oxo-1,3,6,7,8,9-hexahydronaphtho[1,2-c]furan-5-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; hydrogen In 1,2-dichloro-ethane at 20℃; for 16.17h; Inert atmosphere; | 98% |
methyl propargyl alcohol
3-oxo-3-phenylpropionanilide
3-benzoyl-4-methyl-1-phenyl-2-pyridone
Conditions | Yield |
---|---|
With 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine; ruthenium(IV) oxide hydrate; oxygen In tetrahydrofuran under 760.051 Torr; for 12h; Reflux; regioselective reaction; | 98% |
methyl propargyl alcohol
methanesulfonyl chloride
but-2-yn-1-yl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 2h; | 97% |
With triethylamine In dichloromethane | 96% |
With triethylamine In dichloromethane at -20℃; for 0.5h; | 87% |
methyl propargyl alcohol
N-(Benzyloxycarbonyl)glycine
benzyloxycarbonylamino-acetic acid but-2-ynyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 22h; | 97% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; |
methyl propargyl alcohol
Conditions | Yield |
---|---|
With disulfur dichloride; triethylamine In diethyl ether at -10℃; for 0.5h; | 97% |
methyl propargyl alcohol
5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester
5-bromo-2-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid
Conditions | Yield |
---|---|
Stage #1: methyl propargyl alcohol; 5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; water Heating / reflux; Stage #3: With hydrogenchloride In tetrahydrofuran; methanol; water | 97% |
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