Imidazole → HCID 58018637, compound

HRID 1027397Notes

Reaction equation

HRID 1027397 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[C:18]([Si:22](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:21])([CH3:20])[CH3:19].O>ClCCl>[CH2:11]([O:10][C:8]([CH:5]1[CH2:4][CH2:3][CH:2]([O:1][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:7][CH2:6]1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 58018637HCID 58018637, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-hydroxycyclohexane carboxylate (5 g, 29.03 mmol) in dichloromethane (200 mL) was added imidazole (4.97 g, 73 mmol) and tert-butylchlorodiphenylsilane (15.96 g, 15.2 mL, 58 mmol). The reaction mixture was allowed to stir at room temperature over night. The reaction mixture was poured into water (125 mL) in a separatory funnel and the phases were separated. The aqueous phase was extracted with dichloromethane (2×200 mL). The combined organic solutions were washed with brine, dried over Na2SO4, and concentrated under vacuum. Purification by column chromatography on silica gel eluting with ethyl acetate in heptanes (0-10%) afforded 10.55 g (89%) of the title compound.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with dichloromethane (2×200 mL)
  3. washThe combined organic solutions were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customPurification by column chromatography on silica gel eluting with ethyl acetate in heptanes (0-10%)

Sources & evidence

ORD record
ord-8fb9f724b97041e9b185b50a728be56c
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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