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3-Octyn-1-ol Basic information Product Name: 3-Octyn-1-ol Synonyms: 3-OCTYNE-1-OL;3-OCTYN-1-OL;TIMTEC-BB SBB009106;octynol;N-BUTY
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inquiry3-Octyn-1-ol CAS NO.14916-80-4 Application:3-Octyn-1-ol CAS NO.14916-80-4
oct-3-yn-1-ol
Conditions | Yield |
---|---|
With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite at 20℃; for 18h; Green chemistry; chemoselective reaction; | 93% |
2-(3-octyn-1-yloxy)tetrahydro-2H-pyran
oct-3-yn-1-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol; water at 23℃; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate In diethyl ether; ammonia from -30 to 20 deg C, 15 h; | 65% |
Conditions | Yield |
---|---|
With lithium; ferric nitrate In tetrahydrofuran; ammonia for 3h; | 62.2% |
Stage #1: 3-Butyn-1-ol With lithium amide; ammonia; ferric nitrate at -50℃; for 1h; Stage #2: 1-bromo-butane for 2h; Further stages.; | 26.6% |
With lithium amide In ammonia | |
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium 1.) THF, hexane, -23 deg C --> r.t., 30 min, 2.) -23 deg C, 4 h; Yield given. Multistep reaction; | |
With lithium amide; ammonia; ferric nitrate |
Conditions | Yield |
---|---|
With ammonia |
Conditions | Yield |
---|---|
(i) Na, liq. NH3, Fe(NO3)3, (ii) /BRN= 102378/; Multistep reaction; | |
Stage #1: hex-1-yne With ethylmagnesium bromide In tetrahydrofuran Reflux; Stage #2: oxirane In tetrahydrofuran at 20℃; |
1-vinyloxy-oct-3-yne
oct-3-yn-1-ol
Conditions | Yield |
---|---|
With hydrogenchloride |
oxirane
C4H7BrMg
A
oct-3-yn-1-ol
B
oct-3-yn-2-ol
Conditions | Yield |
---|---|
In benzene 12 h, RT; 4 h, reflux; |
Conditions | Yield |
---|---|
With lithium 1) THF, reflux, 2) DMSO, 60 - 65 deg C, 3h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; n-butyllithium; 2,2,6,6-tetramethylpiperidinyl-lithium; cyclohexa-1,3-diene 1.) THF, hexane, -90 deg, 5 min; 2.) THF, hexane, -90 deg C, then Rt, 30 min; 3.) THF, hexane, reflux, 60 min; 4.) THF, hexane, MeOH, 0 deg C, 30 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With diethyl ether | |
With diethyl ether |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Na, liq. NH3 2: aq. HCl View Scheme |
oxirane
hexenylmagnesium bromide
A
oct-3-yn-1-ol
B
2-bromoethanol
oct-3-yn-1-ol
oct-7-yn-1-ol
Conditions | Yield |
---|---|
With sodium hydride In ethylenediamine; mineral oil at 45 - 65℃; | 100% |
With potassium hydride; Trimethylenediamine for 18h; Ambient temperature; | 97% |
With potassium tert-butylate; lithium In ethylenediamine at 25℃; for 3h; | 96% |
oct-3-yn-1-ol
methanesulfonyl chloride
oct-3-yn-1-yl methanesulfonate
Conditions | Yield |
---|---|
Stage #1: oct-3-yn-1-ol With triethylamine In dichloromethane at 0℃; for 1h; Stage #2: methanesulfonyl chloride In dichloromethane at 0 - 20℃; for 2h; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | |
With triethylamine In dichloromethane at -10℃; for 0.5h; Inert atmosphere; | |
With triethylamine In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere; |
oct-3-yn-1-ol
cis-3-octen-1-ol
Conditions | Yield |
---|---|
With dmap; palladium(II) tetraphenylporphyrin; hydrogen In pyridine at 25℃; under 760.051 Torr; for 4h; stereoselective reaction; | 99% |
With quinoline; hydrogen; Lindlar's catalyst In various solvent(s) at 20℃; under 760.051 Torr; for 2h; | 96% |
With sodium tetrahydroborate; hydrogen; nickel(II) acetate tetrahydrate In ethanol at 20℃; for 12h; | 96% |
oct-3-yn-1-ol
1-hydroxyoctan-4-one
Conditions | Yield |
---|---|
With hexafluoroantimonic acid; AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); water at 120℃; for 24h; | 99% |
With water; mercuric triflate In acetonitrile at 20℃; for 0.0833333h; regioselective reaction; | 82% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 23℃; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In diethyl ether | 96% |
In diethyl ether | 96% |
oct-3-yn-1-ol
oct-3-ynoic acid
Conditions | Yield |
---|---|
With Jones reagent In acetone at 0℃; for 0.25h; | 95.1% |
With Jones reagent In acetone at 0℃; for 3h; Inert atmosphere; | 55% |
With chromium(VI) oxide; sulfuric acid; acetone |
oct-3-yn-1-ol
(E)-oct-3-en-1-ol
Conditions | Yield |
---|---|
With ammonia; lithium; tert-butyl alcohol In tetrahydrofuran at -36℃; for 2h; | 95% |
With lithium aluminium tetrahydride In tetrahydrofuran; diethylene glycol dimethyl ether Heating; | 93% |
With ammonia; lithium; tert-butyl alcohol In tetrahydrofuran at -36℃; for 2h; | 88% |
oct-3-yn-1-ol
p-toluenesulfonyl chloride
oct-3-ynyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With pyridine 1) -5 deg C, 0.5 h, 2) 0 deg C, 6 h; | 93% |
In pyridine at 0℃; for 5h; | |
With pyridine or Li-salt of the corresponding acetylenic alcohol; |
oct-3-yn-1-ol
octanol
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In various solvent(s) at 20℃; under 760 Torr; for 5h; | 93% |
oct-3-yn-1-ol
4-methoxy-phenyl-sulphonyl chloride
oct-3-ynyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; | 93% |
oct-3-yn-1-ol
chloromethyl methyl ether
1-(methoxymethoxy)oct-3-yne
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; Inert atmosphere; | 93% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 20h; | 45% |
oct-3-yn-1-ol
tert-butyldimethylsilyl chloride
tert-butyldimethyl(oct-3-yn-1-yloxy)silane
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 23℃; Inert atmosphere; | 93% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; | 22% |
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 0.25h; Inert atmosphere; | 93% |
oct-3-yn-1-ol
2-diazo-3-oxo-3-phenyl-propionic acid methyl ester
methyl (E)-2-benzoyl-3-pentylidenetetrahydrofuran-2-carboxylate
Conditions | Yield |
---|---|
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; zinc(II) chloride In dichloromethane at 20℃; for 7.5h; Molecular sieve; Reflux; stereoselective reaction; | 88% |
oct-3-yn-1-ol
1-hydroxy-3-octanone
Conditions | Yield |
---|---|
With AuCl*C33H53OP; C33H53OP*AuCl; water; silver trifluoromethanesulfonate In methanol at 80℃; for 17h; | 86% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; | 84% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 83% |
Conditions | Yield |
---|---|
Stage #1: oct-3-yn-1-ol; trimethylaluminum In dichloromethane; toluene at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane; toluene at -45℃; for 0.05h; Inert atmosphere; regioselective reaction; | 73% |
Stage #1: oct-3-yn-1-ol; trimethylaluminum In dichloromethane at 0℃; Stage #2: With titanium tetrachloride In dichloromethane at -78℃; for 2h; | 47% |
With titanium tetrachloride In dichloromethane at -45℃; for 0.0166667h; | 75 % Chromat. |
oct-3-yn-1-ol
1-bromo-oct-3-yne
Conditions | Yield |
---|---|
With N-Bromosuccinimide; triphenylphosphine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h; | 71% |
With pyridine; diethyl ether; phosphorus tribromide | |
With triphenyl phosphite; bromine In pyridine; diethyl ether | |
Multi-step reaction with 2 steps 1: 93 percent / pyridine / 1) -5 deg C, 0.5 h, 2) 0 deg C, 6 h 2: 85 percent / LiBr / acetone / 6 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: pyridine / 5 h / 0 °C 2: NaBr / dimethylformamide / 2 h / 75 °C View Scheme |
oct-3-yn-1-ol
4-nitro-2,6-di-tert-butylphenol
3-octynyl aci-nitronate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 8h; | 70% |
Conditions | Yield |
---|---|
Stage #1: ethylenediamine With sodium hydride at 0 - 60℃; for 1h; Inert atmosphere; Stage #2: oct-3-yn-1-ol at 60℃; for 1h; Inert atmosphere; | 58% |
Conditions | Yield |
---|---|
With 1,3-bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene In tetrahydrofuran Inert atmosphere; Molecular sieve; | 52% |
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at 0 - 20℃; for 16h; | 46% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; | 44% |
oct-3-yn-1-ol
p-methoxybenzyl chloride
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; | 35% |
With sodium hydride |