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

HRID 1588956Notes

Reaction equation

HRID 1588956 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f149e6644a4641f599e9a9447691de2b
Source dataset
uspto-grants-1993_06
Patent number
US05223620

Reaction notes

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