Thionyl Chloride → 4-{[(2-Chloromethyl-3-phenyl-1-benzofuran-6-yl)oxy]methyl}-5-methyl-2-phenyl-1,3-oxazole

HRID 2221529Notes

Reaction equation

HRID 2221529 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:31]=[CH:30][C:18]2[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:20]([CH2:22]O)[O:21][C:17]=2[CH:16]=1.S(Cl)([Cl:34])=O.C(=O)([O-])O.[Na+]>>[Cl:34][CH2:22][C:20]1[O:21][C:17]2[CH:16]=[C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[O:6][C:2]=3[CH3:1])[CH:31]=[CH:30][C:18]=2[C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 69215994{6-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methanol

Product 1

HCID 692170184-{[(2-Chloromethyl-3-phenyl-1-benzofuran-6-yl)oxy]methyl}-5-methyl-2-phenyl-1,3-oxazoleYield 92%

Procedure

{6-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methanol (1.50 g) was added to thionyl chloride (5 mL) at 0° C., and the mixture was stirred for 1 hr. After concentration of the reaction mixture, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-{[(2-chloromethyl-3-phenyl-1-benzofuran-6-yl)oxy]methyl}-5-methyl-2-phenyl-1,3-oxazole as colorless crystals (1.43 g, yield 92%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 129-130° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89df89497989477098ddcefbe9081339
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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