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

HRID 1588956노트

반응식

HRID 1588956 반응식
[CH:1]1([OH:8])[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:9]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C.O>CN(C)C=O.CN(C)C1C=CN=CC=1.CCOCC>[Si:13]([O:7][CH:4]1[CH2:5][CH2:6][CH:1]([OH:8])[CH2:2][CH2:3]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:15])[CH3:14]

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 111621,4-CyclohexanediolHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 554539cis-4-((t-Butyldimethylsilyl)oxy)cyclohexan-1-ol수율 35.9%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 1,4-cyclohexandiol (cis: trans=ca. 1:1, 25.0 g) and t-butylchlorodimethylsilane (32.4 g) in dimethylformamide (150 ml) was added slowly and dropwise a solution of triethylamine 21.8 g) and 4-(dimethylamino)pyridine (1.05 g) in dimethylformamide (50 ml) at 0° C. After stirring for one hour, to the reaction mixture were added water and ether. The ether layer was separated, washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by column chromatography (support; silica gel, 300 g, developing agent; ethyl acetate : hexane=1:5) to obtain the object compound (17.8 g) as a mixture of cis and trans isomers (ca. 1:1).

후처리

  1. customat 0° C
  2. customThe ether layer was separated
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by column chromatography (support; silica gel, 300 g, developing agent; ethyl acetate : hexane=1:5)

출처 및 근거

ORD 기록
ord-f149e6644a4641f599e9a9447691de2b
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223620

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