Diethyl Ether → HCID 53758006, compound

HRID 1679511Notes

Reaction equation

HRID 1679511 reaction equation
C([C:4]([Cl:29])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH3:20])[CH3:19])=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)C.[OH-].[Ba+2].[OH-].CCOCC>C(O)C>[Cl:29][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH3:19])[CH3:20])=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6093286Barium hydroxideHCID 54458419HCID 54458419, compound

Product 1

HCID 53758006HCID 53758006, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 3 ml of absolute ethanol, 400 mg of ethyl 2-acetyl-2-chloro-3-[4-(2-benzoyl-2-propyloxy)phenyl]propionate is dissolved and with stirring under ice-cooling, 85 mg of barium hydroxide (dehydrated at 125° C for 8 hours under reduced pressure) is added. After 10 minutes stirring, ether is added and the insoluble material is filtered away. The ether layer is washed with water thoroughly, dried, and the evaporation of the solvent gives the oily product of ethyl 2-chloro-3-[4-(2-benzoyl-2-propyloxy)-phenyl]propionate. In IR and NMR, this product is in good agreement with the compound No. 1 in Example 7.

Workup

  1. temperaturecooling
  2. stirringAfter 10 minutes stirring
  3. filtrationthe insoluble material is filtered away
  4. washThe ether layer is washed with water thoroughly
  5. customdried
  6. customthe evaporation of the solvent

Sources & evidence

ORD record
ord-d2412911ff4849eeabb55d7686cf04f3
Source dataset
uspto-grants-1978_03
Patent number
US04080505

Reaction notes

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