Imidazole → 1-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-
Reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].N1C=CN=C1.[C:12]([Si:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:15])([CH3:14])[CH3:13]>C1COCC1>[C:12]([Si:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])([CH3:15])([CH3:13])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1,4-butanediol (4.0 g, 44.4 mmol) in 250 mL THF was added imidazole (3.7 g, 54.3 mmol) followed by tert-butyl(chloro)diphenylsilane (10 g, 36.4 mmol) at room temperature. The mixture was stirred for 3 h and then quenched by the addition of saturated aqueous NH4Cl (200 mL) and then diluted with ethyl acetate (200 mL). The mixture was extracted with ethyl acetate (3×200 mL) and the combined organic layers washed with brine (3×60 mL) and dried over Na2SO4. The solvent was evaporated and the product isolated by flash column chromatography eluting with 0 to 50% EtOAc/hexanes to give 10.6 g of the title compound as a colorless oil.
Workup
- customquenched by the addition of saturated aqueous NH4Cl (200 mL)
- additiondiluted with ethyl acetate (200 mL)
- extractionThe mixture was extracted with ethyl acetate (3×200 mL)
- washthe combined organic layers washed with brine (3×60 mL)
- dry with materialdried over Na2SO4
- customThe solvent was evaporated
- customthe product isolated by flash column chromatography
- washeluting with 0 to 50% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-b52a38e3ec7b4cc1a5f84fa84cd6305b
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
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