Water → 1-[2-(Benzyloxy)phenyl]-1-(6-phenylpyridin-2-yl)ethanol

HRID 1037662Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH3:30].[Li+].[Br-].O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)([OH:16])[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -90 °C

Procedure

To a solution of 11.7 g (32.0 mmol) of 17 in 260 mL of THF, 37 mL (33.6 mmol) of 0.91 M MeLi*LiBr in THF was added dropwise with vigorous stirring for 20 min at −90° C. The reaction mixture was slowly warmed to room temperature and 50 mL of water was added. The organic solvent was evaporated using a rotary evaporator. The crude product was extracted from the residue with 2×100 mL of dichloromethane. The combined extract was dried over Na2SO4 and then evaporated to dryness. This procedure gave 12.0 g (98%) of 18.

Workup

additionwas added dropwise
temperatureThe reaction mixture was slowly warmed to room temperature
customThe organic solvent was evaporated
customa rotary evaporator
extractionThe crude product was extracted from the residue with 2×100 mL of dichloromethane
extractionThe combined extract
dry with materialwas dried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-fdb267799d9f4677b98874ccdeaba004
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546501B2

Reaction notes

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