Imidazole → [4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanol

HRID 2070604Notes

Reaction equation

HRID 2070604 reaction equation
[CH:1]1([CH2:9][OH:10])[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.[Br-].[Li+]>CN(C)C=O>[Si:15]([O:8][CH2:7][CH:4]1[CH2:5][CH2:6][CH:1]([CH2:9][OH:10])[CH2:2][CH2:3]1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 77351,4-CyclohexanedimethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 82050Lithium Bromide

Product 1

HCID 10753723[4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclohexyl]methanolYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclohexane-1,4-dimethanol (10.0 g) in N,N-dimethylformamide (100 mL) were added successively tert-butyldimethylchlorosilane (8.9 g) and imidazole (9.5 g), followed by stirring the reaction mixture at room temperature for 16 hours. To the reaction mixture were added ice and saturated aqueous lithium bromide solution, followed by extraction with diethyl ether. The organic layer was washed with saturated aqueous lithium bromide solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:9 to 2:3) to give [4-(tert-butyldimethylsilanyloxymethyl)-cyclohexyl]-methano 1 (8.7 g).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe organic layer was washed with saturated aqueous lithium bromide solution and saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:9 to 2:3)

Sources & evidence

ORD record
ord-72f6a98c68994e669277ac8ac7d92b24
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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