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

HRID 1173181

Reaction equation

HRID 1173181 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c8816731a86148869c9f53f8a24c26a3
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Linked notes

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