Triphenylphosphine → 3-(3-Fluoro-phenyl)-2-(2-oxoethyl)-pentanedioic acid 1-methyl ester

HRID 2289165Notes

Reaction equation

HRID 2289165 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH2:17][CH:18]=C)[CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8].[O:21]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH2:17][CH:18]=[O:21])[CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 544686422-Allyl-3-(3-fluoro-phenyl)-pentanedioic acid 1-methyl ester

Product 1

HCID 541186013-(3-Fluoro-phenyl)-2-(2-oxoethyl)-pentanedioic acid 1-methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-allyl-3-(3-fluoro-phenyl)-pentanedioic acid 1-methyl ester (2-5) (1.01 g, 3.28 mmol) and Sudan Red B (0.01 g) in 100 mL CH2Cl2 was treated with ozone at -78° C. for 20 min. Then excess ozone was purged with argon, followed with the addition of PPh3 (2.00 g, 7.63 mmol). The mixture was stirred for 30 min and concentrated under diminished pressure. The residue was purified by flash silica chromatography (EtOAc/Hexane, 1:3) to provide the desired product as two separated pairs of enantiomers (2-6A and 2-6B).

Workup

  1. customThen excess ozone was purged with argon
  2. concentrationconcentrated under diminished pressure
  3. customThe residue was purified by flash silica chromatography (EtOAc/Hexane, 1:3)

Sources & evidence

ORD record
ord-1fb691c82ad247aa86eb9b720d7c8766
Source dataset
uspto-grants-2000_07
Patent number
US06090944

Reaction notes

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