反応式
[OH:1][CH2:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C>[Si:23]([O:1][CH2:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]参加物
5
実験手順
To an ice cooled solution of methyl 3-(4-hydroxy-3-oxo-butyl)phenylacetate (472 mg, 2.00 mmol) in DMF (10 ml) was added imidazole (264 mg, 3.88 mmol) followed by tert-butyldimethylsilyl chloride (408 mg, 5.99 mmol). After 30 minutes the ice-bath was removed and then the mixture was stirred overnight at room temperature. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo. The residue was purified by silica gel (20 g) column chromatography eluting with hexane/ethyl acetate (10:1) to give methyl 3-[4-(tert-butyldimethylsilyloxy)-3-oxobutyl]phenylacetate (664 mg, 94.9%) as a colorless oil.
後処理
- customAfter 30 minutes the ice-bath was removed
- additionThe reaction mixture was poured into water (100 ml)
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried (magnesium sulfate)
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel (20 g) column chromatography
- washeluting with hexane/ethyl acetate (10:1)
出典と根拠
- ORDレコード
- ord-b774a9a2e1924066b5eae6f3b0d8fa73
- 出典データセット
- uspto-grants-2002_03
- 特許番号
- US06359145B1
関連ノート
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