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

HRID 1588956ノート

反応式

HRID 1588956 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f149e6644a4641f599e9a9447691de2b
出典データセット
uspto-grants-1993_06
特許番号
US05223620

反応ノート

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