HCID 57973280, compound → HCID 57973286, compound

HRID 1863891Notes

Reaction equation

HRID 1863891 reaction equation
C([O:8][C:9]([C:11]1([C:24]([O:26]CC2C=CC=CC=2)=[O:25])[CH2:16][CH2:15][P:14](=[O:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[O:23]=[P:14]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:16][C:11]([C:9]([OH:10])=[O:8])([C:24]([OH:26])=[O:25])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 57973280HCID 57973280, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57973286HCID 57973286, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 500 mL Parr flask was added 1-oxo-1-phenyl-1λ5-phosphinane-4,4-dicarboxylic acid dibenzyl ester (8.5 g, 18 mmol), ethanol (250 mL), and palladium on carbon (10%, 1.1 g). The flask was charged with hydrogen (51 psi), and agitated on a mechanical shaker. After 1 hour, the ballast was re-charged to 50 psi (from 40 psi) and shaking continued overnight (14 hours). The reaction mixture was filtered and the solvent removed in vacuo to provide 1-oxo-1-phenyl-1λ5-phosphinane-4,4-dicarboxylic acid (1.8 g, 35%) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 7.9-7.4 (m, 5H), 2.6 -1.4 (m, 8H); ESMS m/z: found, 283 (M+1)+.

Workup

  1. additionthe ballast was re-charged to 50 psi (from 40 psi)
  2. stirringshaking continued overnight (14 hours)
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-42a214e0dd4144a5842b6b15ab7b3cbd
Source dataset
uspto-grants-2009_12
Patent number
US07625880B2

Reaction notes

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