Imidazole → Diethyl 3-(tert-butyldiphenylsiloxy)glutarate

HRID 2249286

反応式

HRID 2249286 の反応式
[OH:1][CH:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CN=C1.O>CN(C)C=O.ClCCl.CCCCCC>[O:1]([CH:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 96259Diethyl 3-hydroxyglutarate

生成物 1

HCID 19825423Diethyl 3-(tert-butyldiphenylsiloxy)glutarate収率 96.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226440Methylenechloride Hexane溶媒

実験手順

To a solution of 1.22 g (5.97 mmol) of diethyl 3-hydroxyglutarate in dry dimethylformamide (30 ml) were added 1.95 g (7.09 mmol) of tert-butyldiphenylsilyl chloride and 1.41 g (20.7 mmol) of imidazole in an atmosphere of argon, and the mixture was allowed to react at room temperature for 10 hours. To the solution was added water followed by extraction with benzene. The organic layer was washed with water and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. From the eluate with dichloromethane-hexane (1:1) was afforded 2.54 g (5.75 mmol) of diethyl 3-(tert-butyldiphenylsiloxy)glutarate.

後処理

  1. customto react at room temperature for 10 hours
  2. extractionfollowed by extraction with benzene
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas subjected to silica gel column chromatography for separation and purification

出典と根拠

ORDレコード
ord-b137e4dd1add486fa79b10bc2fba854c
出典データセット
uspto-grants-1991_08
特許番号
US05043142

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