Imidazole → Diethyl 3-(tert-butyldiphenylsiloxy)glutarate

HRID 2249286

반응식

HRID 2249286 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 19825423Diethyl 3-(tert-butyldiphenylsiloxy)glutarate수율 96.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21226440Methylenechloride Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b137e4dd1add486fa79b10bc2fba854c
출처 데이터셋
uspto-grants-1991_08
특허 번호
US05043142

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