Diethyl Ether → HCID 19074104, compound

HRID 964917Notes

Reaction equation

HRID 964917 reaction equation
[CH3:1][O-].[Na+].[Cl:4][C:5]([F:12])([F:11])[C:6]([O:8]CC)=O.[CH3:13][C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15].CCO[CH2:22][CH3:23]>>[Cl:4][C:5]([F:11])([F:12])[C:6](=[O:8])[CH2:13][C:14]([CH:16]1[CH2:18][CH2:17][CH2:23][CH2:22][CH2:1]1)=[O:15]

Participants

5

Reactant 4

HCID 3283Diethyl Ether3×HCID 13004Cyclopropyl methyl ketoneHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 19074104HCID 19074104, compound

Conditions

Temperature
0 °C

Procedure

74.8 g of sodium methoxide was added to 1 l of ether, and a solution of 200 g of ethyl chlorodifluoroacetate in 300 ml of ether was added dropwise thereto under stirring at 0° C. Then, a solution of 106 g of cyclopropyl methyl ketone in 300 ml of ether was gradually added to the reaction solution, and after the addition, the mixture was stirred at room temperature for 8 hours. The solvent was distilled off under reduced pressure, 300 ml of 6N hydrochloric acid was added to the residue, and extraction with ethyl acetate was carried out. The extract layer was washed with water, and the solvent was distilled off under reduced pressure to obtain 235.9 g of the desired product as a pale yellow liquid. nD20.6 1.4788

Workup

  1. additionafter the addition
  2. stirringthe mixture was stirred at room temperature for 8 hours
  3. distillationThe solvent was distilled off under reduced pressure, 300 ml of 6N hydrochloric acid
  4. additionwas added to the residue, and extraction with ethyl acetate
  5. washThe extract layer was washed with water
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3a257ab3cfec4f8e90d01d36c96aca05
Source dataset
uspto-grants-1998_06
Patent number
US05773388

Reaction notes

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