Acetone → 2-(1-{5-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile

HRID 1690749Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([CH2:16][C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[CH:14]=[N:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:35][C:36]([CH3:38])=[O:37]>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([CH:16]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[C:36]([OH:37])([CH3:38])[CH3:35])[CH:14]=[N:13][CH:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

2-{5-[2-(tert-Butyldimethylsilanyloxy)-ethyl]-imidazol-1-ylmethyl}-benzonitrile (1.14 g, 3.34 mmol) is dissolved in THF (20 mL) and cooled to −78° C. LHMDS (1M in THF, 5 mL, 5 mmol) is added dropwise. Ten min after the end of addition, acetone (0.295 g, 5.01 mmol) is added. The reaction mixture is stirred at −78° C. for 40 min. It is then quenched with saturated aqueous sodium bicarbonate (10 mL). The mixture is allowed to warm to room temperature, then poured into water. After extraction with ethyl acetate the organic phase is dried over Na2SO4 and concentrated in vacuo to give 2-(1-{5-[2-(tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile; MS (ESI) m/z 400.3 (M+H)

Workup

additionis added
customIt is then quenched with saturated aqueous sodium bicarbonate (10 mL)
temperatureto warm to room temperature
additionpoured into water
extractionAfter extraction with ethyl acetate the organic phase
dry with materialis dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8475d40bbd5f46ce8da91fe6814838c2
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153674B2

Reaction notes

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