Imidazole → HCID 69264442, compound

HRID 899260Notes

Reaction equation

HRID 899260 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:11])[CH2:9][OH:10].N1C=CN=C1.[Si:17](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl.CN(C)C=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:11])[CH2:9][O:10][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 555716HCID 555716, compound

Product 1

HCID 69264442HCID 69264442, compoundYield 68.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

To a stirred solution of 1-(2-bromophenyl)ethane-1,2-diol (step 1, 5.01 g, 22.6 mmol) and in dichloromethane (20 mL) and imidazole (2.31 g, 33.9 mmol) in N,N-dimethylformamide (20 mL) was added tert-butyldiphenylsilyl chloride (6.53 g, 23.8 mmol) at 0° C. and the mixture was stirred for 19 h at the same temperature. The reaction mixture was diluted with toluene/ethyl acetate (1/3), then washed with water for three times and brine, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (100 g) eluting with hexane/ethyl acetate (10/1) to afford 7.05 g (68%) of the title compound as a colorless syrup:

Workup

  1. washwashed with water for three times and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel (100 g)
  5. washeluting with hexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-6f1f6f3a3266474b84e2d32e2faaeaa7
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

Loading…