Diethyl Ether → 1,1-Dimethylethyl 2-chloro-3-(4-chlorophenyl)-oxirane carboxylate

HRID 1376833Notes

Reaction equation

HRID 1376833 reaction equation
Cl[CH:2]([Cl:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.CCOCC.[Cl-].[Na+]>O1CCCC1.O>[Cl:10][C:2]1([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[CH:16]([C:15]2[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=2)[O:17]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 77264-ChlorobenzaldehydeHCID 30164831,1-Dimethylethyl dichloroacetate

Product 1

HCID 229169011,1-Dimethylethyl 2-chloro-3-(4-chlorophenyl)-oxirane carboxylateYield 21.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

5.55 g of tert.-butyl dichloroacetate in 30 ml of tetrahydrofuran were stirred while 4.64 g of 4-chlorobenzaldehyde were added, and after cooling to -20° C., 30 ml of an N solution of potassium tert.-butylate in tetrahydrofuran were added. The temperature was allowed to rise to 20° C. and after 20 minutes, 50 ml of ether and 40 ml of water saturated with sodium chloride were added, with stirring for 5 minutes. The decanted organic phase was washed with water saturated with sodium chloride, then dried and concentrated to dryness under reduced pressure. The residue was chromatographed on silica and eluted with methylene chloride to obtain 1.90 g of 1,1-dimethylethyl 2-chloro-3-(4-chlorophenyl)-oxirane carboxylate.

Workup

  1. additionwere added
  2. washThe decanted organic phase was washed with water saturated with sodium chloride
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was chromatographed on silica
  6. washeluted with methylene chloride

Sources & evidence

ORD record
ord-e732cd25f67246d498489bc149eae694
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

Loading…