Benzaldehyde → [4-(tert-Butyldimethylsilanyloxymethyl)-3-methoxyphenyl]-phenylmethanol

HRID 1872700Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][C:11]=1[O:17][CH3:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]CCCC.[CH:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[OH:31])=[CH:12][C:11]=1[O:17][CH3:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To 2-(tert-Butyldimethylsilanyloxymethyl)-5-bromoanisole (500 mg, 1.51 mmol) in THF (10 ml) at -78° C. was added n-BuLi (1.13 ml of a 1.6M solution in penthane, 1.81 mmol) and the mixture allowed to stir for 1 h at -78° C. Benzaldehyde (176 mg, 1.66 mmol) was added and the mixture allowed to warm to room temperature and stirred for 1 h. Water (20 ml) was added and the mixture extracted with ether (3×10 ml). The combined extracts were washed with water (10 ml), brine (10 ml), dried (Na2SO4) and evaporated under reduced pressure. The resulting residue was purified by chromatography (SiO2, 50% ether/petrol) to give the title compound as a colourless oil (303 mg, 56%).

Workup

temperatureto warm to room temperature
stirringstirred for 1 h
extractionthe mixture extracted with ether (3×10 ml)
washThe combined extracts were washed with water (10 ml), brine (10 ml)
dry with materialdried (Na2SO4)
customevaporated under reduced pressure
customThe resulting residue was purified by chromatography (SiO2, 50% ether/petrol)

Sources & evidence

ORD record: ord-43d3cb099729434d95669f67ecfa2b21
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110934

Reaction notes

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