ethyl 4-diethoxyphosphoryl-3-oxobutanoate → HCID 54162917, compound

HRID 488072Notes

Reaction equation

HRID 488072 reaction equation
[CH2:1]([O:3][P:4]([O:15][CH2:16][CH3:17])([CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2]>CO.O=[Pt]=O>[CH2:16]([O:15][P:4]([O:3][CH2:1][CH3:2])([CH2:6][CH:7]([OH:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:17]

Participants

4

Reactant 1

HCID 11129233ethyl 4-diethoxyphosphoryl-3-oxobutanoate

Product 1

HCID 54162917HCID 54162917, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

The title compound of Example 7 (17 g, 63.8 mmol) was dissolved in 200 mL of methanol. To this solution was added PtO2 (1.7 g, 10% w/w). The mixture was degassed by evacuation of air, then refilling with hydrogen. This degassing procedure was repeated three times. The pressure in the Parr-shaker was set to 50 psi, and the mixture was shaken for 36 hours. The catalyst was filtered through a Celite pad and the filtrate was concentrated on a rotavap to give 17.3 g (~100%) of the title compound as a white solid, m.p. 33° C. to 35° C.

Workup

  1. customThe mixture was degassed by evacuation of air
  2. filtrationThe catalyst was filtered through a Celite pad
  3. concentrationthe filtrate was concentrated on a rotavap

Sources & evidence

ORD record
ord-7dc18a2e135f4627b7a63870dc9febcf
Source dataset
uspto-grants-1994_03
Patent number
US05298625

Reaction notes

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