Imidazole → HCID 178501168, compound

HRID 1520715Notes

Reaction equation

HRID 1520715 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19]>ClCCl>[Si:22]([O:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178501147HCID 178501147, compound

Product 1

HCID 178501168HCID 178501168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-methyl 4-(hydroxymethyl)cyclohexanecarboxylate was dissolved in dichloromethane (30 mL), then imidazole (1.0 g) and tert-butylchlorodimethylsilane (1.6 g) were added. The reaction was stirred at room temperature overnight. The reaction mixture was then concentrated, dissolved in ethyl acetate and washed with 1N aqueous HCl, water, and brine. The organic layer was dried over Na2SO4. The title compound was obtained after filtration and concentration.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with 1N aqueous HCl, water, and brine
  4. dry with materialThe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-a42064e3593e4ec6b09a063c034f5812
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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