Bromotrimethylsilane → [5-(Tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanol
Reaction equation
[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:31][O:32]COC)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Br)(C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:22][C:21]=1[CH2:31][OH:32])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
To a mixture of 5-tert-butyldiphenylsilyloxymethyl-4-methoxymethoxymethyl-2-phenyl-1,3-oxazole (20.0 g) and chloroform (250 mL) added dropwise trimethylsilyl bromide (25.0 g) at −40° C. The reaction mixture was stirred at −40° C. for 30 min, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2, v/v) to give [5-(tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanol. Recrystallization from hexane-ethyl acetate gave colorless crystals (10.2 g, yield 56%). melting point: 95-96° C.
Workup
- stirringthe mixture was further stirred at room temperature for 1 hr
- extractionextracted with chloroform
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated
- washeluted with ethyl acetate-hexane (1:2
Sources & evidence
- ORD record
- ord-35551a6a8c6b41a39e3e5918033e8db4
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368578B2
Reaction notes
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