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

HRID 1015968

反応式

HRID 1015968 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-19a6bbf1b07a492584267403306e2d39
出典データセット
uspto-grants-2011_07
特許番号
US07985730B2

関連ノート

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