1,3-Dichloroacetone → 4-Chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole

HRID 2113876Notes

Reaction equation

HRID 2113876 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12]([NH2:14])=[O:13])=[CH:6][CH:5]=1.[Cl:17][CH2:18][C:19]([CH2:21]Cl)=O>C1(C)C=CC=CC=1>[Cl:17][CH2:18][C:19]1[N:14]=[C:12]([CH:11]=[CH:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:15])([F:16])[F:1])=[CH:9][CH:8]=2)[O:13][CH:21]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 27816943-(4-Trifluoromethoxy-phenyl)-acrylamide

Product 1

HCID 690715774-Chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.28 g (18.5 mmol) 3-(4-Trifluoromethoxy-phenyl)-acrylamide, 2.80 g (22.2 mmol) 1,3-dichloroacetone and 30.0 ml toluene were kept at reflux temperature for 16 h with continuous removal of water by use of a Dean-Stark trap. After removal of solvents in vacuo, the residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 20:1). All fractions containing the product were concentrated to a volume of 10 ml and the crystallized material isolated by filtration, washed with cold heptane and dried. 1.75 g (31%) 4-Chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole.

Workup

  1. temperatureat reflux temperature for 16 h
  2. customwith continuous removal of water by use of a Dean-Stark trap
  3. customAfter removal of solvents in vacuo
  4. customthe residue was purified by chromatography on silica gel (eluent: heptane/ethyl acetate 20:1)
  5. additionAll fractions containing the product
  6. concentrationwere concentrated to a volume of 10 ml
  7. customthe crystallized material isolated by filtration
  8. washwashed with cold heptane
  9. customdried

Sources & evidence

ORD record
ord-459092aa475043ed9494588855f5a516
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

Loading…