2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonic Acid, Benzyl Methyl Ester → 2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}-3-methoxy-3-oxopropanoic acid

HRID 566496Notes

Reaction equation

HRID 566496 reaction equation
[C:1]([O:5][P:6]([C:13]([F:59])([F:58])[C:14]1[CH:57]=[CH:56][C:17]([CH2:18][C:19]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([P:44]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([F:43])[F:42])=[CH:37][CH:36]=2)([C:30]([O:32]C)=[O:31])[C:20]([O:22][CH2:23]C2C=CC=CC=2)=[O:21])=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:47]([O:46][P:44]([C:41]([F:42])([F:43])[C:38]1[CH:39]=[CH:40][C:35]([CH2:34][C:19]([CH2:18][C:17]2[CH:16]=[CH:15][C:14]([C:13]([P:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([F:58])[F:59])=[CH:57][CH:56]=2)([C:20]([O:22][CH3:23])=[O:21])[C:30]([OH:32])=[O:31])=[CH:36][CH:37]=1)([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:45])([CH3:48])([CH3:49])[CH3:50]

Participants

4

Reactant 1

HCID 867562362,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonic Acid, Benzyl Methyl Ester

Product 1

HCID 212657292,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}-3-methoxy-3-oxopropanoic acidYield 55.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2,2-di{4-[(di-tert-butoxyphosphoryl) (difluoro)methyl]benzyl}malonic acid, benzyl methyl ester (0.2 g) and Pd/C (0.1 g, 10%) in 30 mL of MeOH was shaken under 50 psi of H2 for 3 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel chromatography eluted with 3:2:0.1 EtOAc/hexane/AcOH to give 0.1 g of the title compound as a yellow syrup.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography
  4. washeluted with 3:2:0.1 EtOAc/hexane/AcOH

Sources & evidence

ORD record
ord-ec8aed18a9794f239a61745c9833374e
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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