Imidazole → HCID 178455371, compound

HRID 1095146

Reaction equation

HRID 1095146 reaction equation
[C@H:1]1([OH:8])[CH2:6][CH2:5][C@H:4]([OH:7])[CH2:3][CH2:2]1.N1C=CN=C1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[C:14]([Si:18]([CH3:21])([CH3:20])[O:7][C@H:4]1[CH2:5][CH2:6][C@H:1]([OH:8])[CH2:2][CH2:3]1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178521615HCID 178521615, compound

Product 1

HCID 178455371HCID 178455371, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of trans-1,4-cyclohexanediol (3 g, 26 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0° C. was added imidazole (1.7 g, 26 mmol) and tert-butyldimethylchlorosilane (3.87 g, 26 mmol). The reaction mixture was then stirred at 0° C. for 1 h. The mixture was partitioned between ethyl acetate and water. Organic layer was separated, aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1;2) to give trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol as a white solid (3.9 g, 65%).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customOrganic layer was separated
  3. extractionaqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:hexanes=1;2)

Sources & evidence

ORD record
ord-2ee3af40792347619c7d449624ac0469
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Linked notes

Loading…