Butanoic acid, 3-oxo-4-(phenylmethoxy)-, 1,1-dimethylethyl ester → HCID 13422882, compound

HRID 2290418Notes

Reaction equation

HRID 2290418 reaction equation
C([O:8][CH2:9][C:10](=[O:19])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][C:10](=[O:19])[CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13]

Participants

4

Reactant 1

HCID 12035485Butanoic acid, 3-oxo-4-(phenylmethoxy)-, 1,1-dimethylethyl ester

Product 1

HCID 13422882HCID 13422882, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 963 mg (5 mmol) of tert.-butyl 4-benzyloxyacetoacetate and 200 mg of palladium (10% on charcoal) in 50 ml of methanol was stirred at room temperature under a hydrogen atmosphere (1 atmosphere) for 1.5 hours. The catalyst was filtered off washed with a little methylene chloride. The filtrate solution was evaporated in vacuo and the residue was filtered through 3 g of neutral aluminum oxide (methylene chloride). The solvent was evaporated off in vacuo and the oil which remained was dried under a high vacuum. 567 mg (65% of tert.-butyl 4-hydroxyacetoacetate were obtained, and were used immediately for further reactions.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with a little methylene chloride
  3. customThe filtrate solution was evaporated in vacuo
  4. filtrationthe residue was filtered through 3 g of neutral aluminum oxide (methylene chloride)
  5. customThe solvent was evaporated off in vacuo
  6. customthe oil which remained was dried under a high vacuum

Sources & evidence

ORD record
ord-f51341f8d7fc416283fa878667acaac7
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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