Propanal → 1,1-Dimethylethyl 2-chloro-3-ethyloxirane carboxylate

HRID 1376827

Reaction equation

HRID 1376827 reaction equation
Cl[CH:2]([Cl:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH:11](=[O:14])[CH2:12][CH3:13].CCOCC.O>O1CCCC1>[Cl:10][C:2]1([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[CH:11]([CH2:12][CH3:13])[O:14]1

Participants

6

Reactant 4

HCID 527PropanalHCID 962WaterHCID 3283Diethyl EtherHCID 30164831,1-Dimethylethyl dichloroacetate

Product 1

HCID 229168041,1-Dimethylethyl 2-chloro-3-ethyloxirane carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

4 ml of tert.-butyl dichloroacetate and 2 ml of propanal diluted with 2 ml of tetrahydrofuran were mixed together and cooled to -20° C. 28 ml of 0.9M/l of potassium tert.-butylate in tetrahydrofuran were introduced over 12 minutes and at -20° C. followed by allowing the temperature to rise to 20° C. over 1 hour 20 minutes. 25 ml of ether and 25 ml of water were added, followed by stirring, decanting, and re-extracting with ether. The organic phase was washed with water saturated with sodium chloride, then dried and concentrated to dryness to obtain 4.7 g of 1,1-dimethylethyl 2-chloro-3-ethyloxirane carboxylate.

Workup

  1. additionwere mixed together
  2. customdecanting
  3. extractionre-extracting with ether
  4. washThe organic phase was washed with water saturated with sodium chloride
  5. customdried
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ee5ef401fd8a4f8bb5b206c69f3b609f
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Linked notes

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