Imidazole → HCID 69987244, compound

HRID 1634732Notes

Reaction equation

HRID 1634732 reaction equation
N1C=CN=C1.[F:6][C:7]1[CH:8]=[C:9]([C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][C:12]=1[OH:13].[C:17]([Si:21]([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)Cl)([CH3:20])([CH3:19])[CH3:18].O>ClCCl>[Si:21]([O:13][C:12]1[CH:11]=[CH:10][C:9]([C:14](=[O:16])[CH3:15])=[CH:8][C:7]=1[F:6])([C:17]([CH3:20])([CH3:19])[CH3:18])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 69987244HCID 69987244, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of imidazole (7.29 g, 107.0 mmol) and 1-(3-fluoro-4-hydroxyphenyl)-1-ethanone (15.0 g, 97.3 mmol) in anhydrous dichloromethane (500 mL) was added drop-wise a solution of t-butyldiphenylchlorosilane (28.09 g, 102.0 mmol) in anhydrous dichloromethane (100 mL). The solution was stirred overnight at room temperature. The mixture was poured into water (500 mL) and the organic layer separated and washed with saturated sodium hydrogen carbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo to give the title compound which was used without further purification (37.9 g, 96.55 mmol). MS (APCI+, m/z): 393 [M+H]+.

Workup

  1. customthe organic layer separated
  2. washwashed with saturated sodium hydrogen carbonate, water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe solution was filtered
  5. customthe solvent evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-28c0c6158f834c21ac5ef3758b073ad8
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…