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Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at -78 - 20℃; | 100% |
Stage #1: n-butyllithium With mischmetall tribromide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78℃; for 3h; Imamoto reaction; | 98% |
In hexane at -78 - 20℃; for 1.16667h; | 95% |
Conditions | Yield |
---|---|
With C28H35ClCoN5(1+)*Cl(1-); potassium tert-butylate; hydrogen In tetrahydrofuran at 20℃; under 22502.3 Torr; for 16h; Autoclave; | 99% |
With (4-NHCpr)Triaz(NHPiPr2)2Mn(CO)2Br; potassium tert-butylate; hydrogen In toluene at 80℃; under 15001.5 Torr; for 4h; Inert atmosphere; Autoclave; | 98% |
With sodium tetrahydroborate In methanol at 20℃; for 2h; | 96% |
Conditions | Yield |
---|---|
Stage #1: 1-bromo-butane With magnesium; lithium chloride In tetrahydrofuran at 50℃; for 0.125h; Flow reactor; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 0.333333h; Flow reactor; | 98% |
Stage #1: 1-bromo-butane With magnesium; ethylene dibromide In 2-methyltetrahydrofuran at 20℃; Inert atmosphere; Stage #2: benzaldehyde In 2-methyltetrahydrofuran at 0 - 20℃; for 1.25h; Grignard reaction; Inert atmosphere; chemoselective reaction; | 86% |
With magnesium 1) Et2O, 40 deg C, 1h, 2) 35 deg C, 1h; Multistep reaction; |
triethyl-butyl plumbane
benzaldehyde
A
1-Phenyl-1-propanol
B
1-Phenyl-1-pentanol
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at -78 - -30℃; | A 98% B 1.7% |
Conditions | Yield |
---|---|
With cerium(III) chloride; lithium hydride In tetrahydrofuran at -78℃; for 72h; | 94% |
cyclopropyl bromide
benzaldehyde
A
1-Phenyl-1-pentanol
B
1-phenyl-1-cyclopropylmethanol
Conditions | Yield |
---|---|
Stage #1: cyclopropyl bromide; tri-n-butyllithium magnesate complex In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78 - -60℃; | A n/a B 91% |
n-butyllithium
1-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-1H-imidazole
1-Phenyl-1-pentanol
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 0.166667h; | 90% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran; water at 20℃; for 20h; Product distribution; Further Variations:; Solvents; amount of water; with additive; | 90% |
With bis(1,5-cyclooctadiene)nickel (0); tri-tert-butyl phosphine; caesium carbonate In tetrahydrofuran; hexane; toluene at 20℃; for 24h; | 86% |
n-butyllithium
1-(Benzyloxy)-5-(trimethylsilyl)pyrazole
A
1-Phenyl-1-pentanol
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 0.166667h; Elimination; addition; | A 88% B 84% |
Conditions | Yield |
---|---|
Stage #1: 2-phenyl-1,3-dioxolane With sodium dodecyl-sulfate; toluene-4-sulfonic acid In tetrahydrofuran; water at 25℃; for 3.5h; Stage #2: lithium di-n-butylcuprate In diethyl ether; hexane at 25℃; for 12h; Further stages.; | 87% |
Stage #1: 2-phenyl-1,3-dioxolane With water; sodium dodecyl-sulfate; toluene-4-sulfonic acid In tetrahydrofuran at 25℃; for 3.5h; Inert atmosphere; polydimethylsiloxane (PDMS) thimble; Stage #2: lithium di-n-butylcuprate In hexanes; diethyl ether for 12h; Stage #3: With water In hexanes; diethyl ether | 87% |
Conditions | Yield |
---|---|
With bis(acetylacetonate)nickel(II) In N,N-dimethyl-formamide at 0 - 50℃; for 12h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; | 87% |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at -30℃; for 0.25h; | 86% |
Conditions | Yield |
---|---|
Stage #1: 1-iodo-butane With N-butylpyridinium tetrafluoroborate at 20℃; for 1h; Stage #2: benzaldehyde With pyridine at 20℃; for 12h; Further stages.; | 80% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; sec.-butyllithium; samarium(III) trifluoromethanesulfonate 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h; Yield given. Multistep reaction; | |
Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Stage #1: Tributyl-((2S,6S)-6-isopropyl-2-phenyl-tetrahydro-pyran-2-yloxymethyl)-stannane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: benzaldehyde In tetrahydrofuran; hexane for 0.5h; Further stages.; | A 17% B 80% |
n-butyllithium
benzaldehyde
A
1-Phenyl-1-pentanol
B
2,2-difluoro-1-phenyl-3-buten-1-ol
Conditions | Yield |
---|---|
With 3-bromo-3,3-difluropropene In tetrahydrofuran; diethyl ether; hexane; pentane at -95℃; | A 78% B n/a |
Conditions | Yield |
---|---|
Stage #1: tributyl borane; 1-benzyl-tetrahydro-thiophenium tetrafluoroborate With lithium hexamethyldisilazane In tetrahydrofuran; 1,4-dioxane at 5℃; for 5h; Stage #2: With sodium hydroxide; dihydrogen peroxide | A 78% B 11% |
Conditions | Yield |
---|---|
With tributyl(2-methoxyethyl)phosphonium bis(CF3SO2)imide In tetrahydrofuran at 0℃; Grignard reaction; | 76% |
n-butyllithium
methyl 2-bromoacrylate
benzaldehyde
A
1-Phenyl-1-pentanol
B
4-hydroxy-4-phenyl-but-2-ynoic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 3h; Inert atmosphere; | A 76% B 6% |
n-butyllithium
2-trimethylsilylbenzaldehyde
1-Phenyl-1-pentanol
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; 2-trimethylsilylbenzaldehyde With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
In diethyl ether for 6h; -20 deg C to 22 deg C; | 72% |
With N,N,N,N,-tetramethylethylenediamine In hexane for 16h; -70 deg C to room temperature; Yield given; |
1-iodo-butane
benzaldehyde
A
1-Phenyl-1-pentanol
B
benzyl alcohol
Conditions | Yield |
---|---|
Stage #1: 1-iodo-butane With 1-butylpyridinium bromide; N-butylpyridinium tetrafluoroborate; zinc at 50℃; for 1h; Stage #2: benzaldehyde at 20℃; for 12h; | A 70% B n/a |
n-butyllithium
benzaldehyde
A
phenyl butyl ketone
B
1-Phenyl-1-pentanol
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; benzaldehyde In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: With N-(tert-butyl)benzenesulfinimidoyl chloride In tetrahydrofuran at -78℃; for 5h; | A 12% B 68% |
With vanadium(III) chloride In dichloromethane for 16h; Product distribution; Heating; var. solvent, temp., time; |
di-n-butylzinc
diethylzinc
benzaldehyde
A
1-Phenyl-1-pentanol
B
(S)-1-phenyl-1-propanol
Conditions | Yield |
---|---|
With catalyst: (-)-3-exo-(dimethylamino)isoborneol In toluene toluene-soln. of catalyst added Bu2Zn at 30°C; after 15 min added Et2Zn; mixt. stirred for 10 min and cooled to 0°C; added benzaldehyde; mixt. stirred at 0°C for 6 h; quenched (water); analyzed by HPLC; | A 14% B 68% |
With catalyst: (-)-3-exo-(dimethylamino)isoborneol In toluene toluene-soln. of catalyst added Et2Zn at 30°C; after 15 min added Bu2Zn; cooled to 0°C; added benzaldehyde; mixt. stirred at 0°C for 6 h; quenched (water); analyzed by HPLC; | A 35% B 44% |
diethylzinc
benzaldehyde
A
1-Phenyl-1-pentanol
B
(S)-1-phenyl-1-propanol
Conditions | Yield |
---|---|
In toluene toluene-soln. of Zn-complex added benzaldehyde; cooled to 0°C; added Et2Zn; mixt. stirred at 0°C for 6 h; quenched (water); analyzed by HPLC; | A 14% B 67% |
In toluene toluene-soln. of Zn-complex added Bu2Zn; mixt. stirred at -78°C; added benzaldehyde; mixt. stirred at 0°C for 6 h; quenched (water); analyzed by HPLC; | A 13% B 66% |
Conditions | Yield |
---|---|
Stage #1: benzoic acid ethyl ester With lithium diisobutyl-tert-butoxyaluminum hydride In tetrahydrofuran; hexane at 0℃; for 3h; Stage #2: butyl magnesium bromide In tetrahydrofuran; diethyl ether; hexane at 20℃; for 0.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether; hexane | 66% |
With lithium borohydride In tetrahydrofuran at 0℃; for 24h; | 61% |
n-butyllithium
benzaldehyde
A
phenylethane 1,2-diol
B
1-Phenyl-1-pentanol
C
benzoic acid
D
benzyl alcohol
Conditions | Yield |
---|---|
Yield given. Multistep reaction; | A 65% B n/a C n/a D 8% E n/a |
Conditions | Yield |
---|---|
With C17H15Cl3N5Ru; potassium hydroxide at 110℃; under 750.075 Torr; for 12h; Inert atmosphere; Sealed tube; Green chemistry; | 65% |
With [(4-(4-CF3)-Ph)Tr(NP(iPr)2)(NHP(iPr)2)Ir(cod)]; potassium tert-butylate In 1,4-dioxane at 125℃; for 4h; Inert atmosphere; Sealed tube; |
Conditions | Yield |
---|---|
With sodium perborate; tert.-butyl lithium In tetrahydrofuran 1.) -78 deg C, 30 min; 2.) r.t., 2 h; | 64% |
n-butyllithium
2-bromo-3,3,3-trifluoropropene
benzaldehyde
A
1-Phenyl-1-pentanol
B
1-phenyl-2-(trifluoromethyl)-2-propen-1-ol
Conditions | Yield |
---|---|
Stage #1: n-butyllithium; 2-bromo-3,3,3-trifluoropropene In diethyl ether at -100℃; for 0.25h; Stage #2: benzaldehyde In diethyl ether at -100℃; for 0.25h; | A 64% B 25% |
Conditions | Yield |
---|---|
With chlorobis(cyclooctene)rhodium(I) dimer; α-Oxo-phenylmethan-diphenylphosphin; sodium carbonate In water; toluene at 60℃; Schlenk technique; Inert atmosphere; | 64% |
Conditions | Yield |
---|---|
With nickel(II) triflate; cyclohexanone; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 110℃; for 12h; Schlenk technique; | 99% |
With Oxone; 3,3'-diiodo-2,2',6,6'-tetramethoxy-4,4'-biphenyldicarboxylic acid In nitromethane; water at 30 - 35℃; for 11.5h; | 98% |
With menthol; Dess-Martin periodane In dichloromethane for 0.333333h; Dess-Martin oxidation; | 95% |
1-Phenyl-1-pentanol
1-bromo-1-phenylpentane
Conditions | Yield |
---|---|
With sulfurous dibromide In toluene for 6h; | 99% |
With pyridine; phosphorus tribromide In diethyl ether for 2.5h; Ambient temperature; | 77% |
With phosphorus tribromide In diethyl ether at 0 - 20℃; | 22% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: 1-Phenyl-1-pentanol With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: trichloroacetonitrile In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: carbon disulfide; 1-Phenyl-1-pentanol With sodium hydride In tetrahydrofuran at 20℃; for 10h; Addition; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h; Methylation; | 95% |
1-Phenyl-1-pentanol
4-sulfanylphenol
1-hydroxy-4-<(1-phenylpentyl)thio>benzene
Conditions | Yield |
---|---|
With zinc(II) iodide In 1,2-dichloro-ethane for 4h; Ambient temperature; | 94% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; | 94% |
Conditions | Yield |
---|---|
With sulfuric acid; nickel In water at 10℃; for 2h; | 92% |
With chloro-trimethyl-silane; acetonitrile; sodium iodide In hexane for 24h; Ambient temperature; | 74% |
With chloro-trimethyl-silane; acetonitrile; sodium iodide In hexane for 24h; Ambient temperature; | 74% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; | 92% |
With pyridine; triethylamine In dichloromethane at 20℃; | 80% |
With triethylamine In dichloromethane |
Conditions | Yield |
---|---|
Stage #1: 1-Phenyl-1-pentanol; benzoic acid With N-Bromosuccinimide In 1,4-dioxane at 60℃; for 1h; Sealed tube; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 60℃; for 4h; | 92% |
Stage #1: 1-Phenyl-1-pentanol; benzoic acid With N-Bromosuccinimide In 1,4-dioxane at 60℃; for 1h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 4h; | 92% |
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; ethyl acetate at 100℃; for 12h; Schlenk technique; | 70% |
1-Phenyl-1-pentanol
<1-(phenylthio)pentyl>benzene
Conditions | Yield |
---|---|
With zinc(II) iodide In 1,2-dichloro-ethane for 0.666667h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With zinc(II) iodide In 1,2-dichloro-ethane for 8h; Ambient temperature; | 90% |
β-mercaptopropionamide
1-Phenyl-1-pentanol
3-<(phenylpentyl)thio>propanamide
Conditions | Yield |
---|---|
With zinc(II) iodide In 1,2-dichloro-ethane for 8h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With oxygen; potassium carbonate at 150℃; under 4500.45 Torr; for 48h; Autoclave; | 90% |
1-Phenyl-1-pentanol
(trifluoromethyl)trimethylsilane
Conditions | Yield |
---|---|
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Glovebox; Inert atmosphere; | 87% |
1-Phenyl-1-pentanol
methyl 4-mercaptobenzoate
methyl 4-<(1-phenylpentyl)thio>benzoate
Conditions | Yield |
---|---|
With zinc(II) iodide In 1,2-dichloro-ethane for 3h; Ambient temperature; | 86% |
1-Phenyl-1-pentanol
para-bromobenzenethiol
1-bromo-4-<(1-phenylpentyl)thio>benzene
Conditions | Yield |
---|---|
With zinc(II) iodide In 1,2-dichloro-ethane for 0.333333h; Ambient temperature; | 86% |
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