Imidazole → Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate

HRID 1160612노트

반응식

HRID 1160612 반응식
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C=O)C.CCOC(C)=O>[Si:22]([O:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 14530758Benzyl 3-hydroxycyclopentanecarboxylate

생성물 1

HCID 68717013Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of benzyl 3-hydroxycyclopentanecarboxylate (1.0 g, 4.54 mmol) in 9 ml of degassed DMF was added imidazole (0.34 g, 4.99 mmol) and tert-butyldimethylsilyl chloride (0.75 g, 4.99 mmol). The mixture was stirred at ambient temperature for 4 hours, and then poured into 70 mL of water, and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water and brine and then dried over sodium sulfate. Filtration and concentration afforded the crude product which was subjected to chromatography on silica gel eluting with 5% EtOAc in hexanes to give benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration
  5. customafforded the crude product which

출처 및 근거

ORD 기록
ord-fe3af9218aee4e8d81d4a254c58e43b1
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816380B2

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