Imidazole → cis-4-((t-Butyldimethylsilyl)oxy)cyclohexan-1-ol

HRID 1015968

반응식

HRID 1015968 반응식
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.N1C=CN=C1.CCN(CC)CC.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl.O>[Si:21]([O:7][CH:4]1[CH2:5][CH2:6][CH:1]([OH:8])[CH2:2][CH2:3]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 111621,4-CyclohexanediolHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 554539cis-4-((t-Butyldimethylsilyl)oxy)cyclohexan-1-ol수율 42.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,4-cyclohexanediol (5 g, 43 mmol), imidazole (2.92 g, 43 mmol) and NEt3 (7 mL) in CH2Cl2 (100 mL) cooled in an ice bath was added tert-butyldimethylsilyl chloride (6.47 g, 43 mmol). The mixture was stirred at room temperature overnight. Water was added and the organic phase was separated. The aqueous layer was extracted with EtOAc. The combined organic phase was dried over MgSO4 and concentrated. Chromatography on silica gel eluting with 3:1 EtOAc/hexanes provided the title compound (4.2 g, 42%) as an oil. MS calculated (M+H)+ 231. found 231.

후처리

  1. customthe organic phase was separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-19a6bbf1b07a492584267403306e2d39
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985730B2

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