p-Toluenesulfonic acid → Ethyl 5,5,5-trifluoro-4-oxopentanoate

HRID 973746Notes

Reaction equation

HRID 973746 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](=[O:16])[CH:4](C(OCC)=O)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].B(O)(O)O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:1][C:2]([F:17])([F:18])[C:3](=[O:16])[CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7628Boric AcidHCID 11346247Butanedioic acid, (trifluoroacetyl)-, diethyl ester

Product 1

HCID 13379932Ethyl 5,5,5-trifluoro-4-oxopentanoateYield 32.7%

Procedure

45 g of the product of Step A, 10.3 g of boric acid and 1 g of p-toluenesulfonic acid were heated at 180° C. for 3 hours and the mixture was poured into ice and extracted with ethyl acetate. The mixture was decanted, dried and concentrated under reduced pressure and the residue was distilled to obtain 10.8 g of expected product.

Workup

  1. additionthe mixture was poured into ice
  2. extractionextracted with ethyl acetate
  3. customThe mixture was decanted
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-83ba7ad84df644098a26a657708b16de
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

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