Imidazole → Benzyl 3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoate
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])=[CH:4][CH:3]=1.N1C=CN=C1.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26]>ClCCl.O>[Si:29]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])=[CH:6][CH:7]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]Participants
6
Procedure
A solution of benzyl 3-(4-hydroxyphenyl)propanoate (1.0 g, 11.70 mmol) in dichloromethane (60 ml) was cooled to 0° C., and imidazole (1.30 g, 18.73 mmol) and tert-butylchlorodimethylsilane (1.94 g, 12.87 mmol) were added thereto, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5) to give the title compound as an oil (4.0 g, yield 95%).
Workup
- extractionwas extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialwas dried over anhydrous sodium sulfate
- customthe filtrate was removed by distillation under reduced pressure
- customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5)
Sources & evidence
- ORD record
- ord-574aeabcf769446d9e3457bf64a55302
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115079B2
Reaction notes
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