Imidazole → HCID 86696723, compound

HRID 1774221Notes

Reaction equation

HRID 1774221 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:26])[CH2:22][CH:23]([OH:25])[CH3:24])=[CH:17][C:16]=1[F:27]>C(Cl)Cl>[Si:10]([O:25][CH:23]([CH3:24])[CH2:22][CH:21]([C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[C:16]([F:27])[CH:17]=1)[OH:26])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86696722HCID 86696722, compound

Product 1

HCID 86696723HCID 86696723, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Imidazole (96.0 mg, 1.42 mmol) and tert-butylchlorodimethylsilane (107 mg, 0.710 mmol) were added to a solution of 1-(4-chloro-3-fluorophenyl)butane-1,3-diol (130 mg, 0.590 mmol) in DCM (10 mL) The resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with DCM (15 mL), washed with brine and water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:4) to afford 3-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)butan-1-ol (130 mg, 66% yield) as oil.

Workup

  1. washwashed with brine and water
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with ethyl acetate/petroleum ether (1:4)

Sources & evidence

ORD record
ord-46b513bbb2554783b9d98439a379ee43
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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