Water → 1-[Cyano(p-benzyloxyphenyl)methyl]cyclohexanol

HRID 1874313Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li].C[Si](N[Si](C)(C)C)(C)C.[C:28]1(=[O:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.O>O1CCCC1>[C:16]([CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)[C:28]1([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)#[N:17]

Participants

Conditions

Temperature: -78 °C

Procedure

p-Benzyloxyphenyl acetonitrile (50 g) was added to dry tetrahydrofuran (250 ml) and cooled to −78° C. Lithium HMDS (20.8 g) in tetrahydrofuran (60 ml) was added slowly to the reaction mixture at −70° C. followed by dropwise addition of cyclohexanone (26.6 g. 0.27 mol) and maintaining the temperature at −60° C. for 2 h. The reaction temperature was allowed to rise to 0° C., charged with water (300 ml) and the organic layer was separated. The aqueous layer was then extracted with ethylacetate. The two organic layers were combined, washed with DM water and dried using Na2SO4. The solvent was evaporated under reduced pressure to give 50 g (70.0%) of 1-[cyano(p-benzyloxyphenyl)methyl]-cyclohexanol.

Workup

temperaturemaintaining the temperature at −60° C. for 2 h
customto rise to 0° C.
customthe organic layer was separated
extractionThe aqueous layer was then extracted with ethylacetate
washwashed with DM water
customdried
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3008680d71564dbfa1e349d723d26a1d
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304578B2

Reaction notes

Loading…