Triphenylphosphine → Hexanoic acid, 3-methyl-6-oxo-, methyl ester, (R)-

HRID 1683997Notes

Reaction equation

HRID 1683997 reaction equation
[O:1]=[O+][O-].[C:4]([O:15][CH3:16])(=[O:14])[CH2:5][CH:6]([CH2:8][CH2:9][CH:10]=C(C)C)[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[CH:10]([CH2:9][CH2:8][C@@H:6]([CH3:7])[CH2:5][C:4]([O:15][CH3:16])=[O:14])=[O:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 61290Methyl 3,7-dimethyloct-6-enoate

Product 1

HCID 11030088Hexanoic acid, 3-methyl-6-oxo-, methyl ester, (R)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ozone generated by a Welsbach Ozonator was passed, at -78° C., into a solution of R(+) methyl citronellate (JACS 1968, 90, 3525; 3.0 g) in MeOH (30 mL) for 1.5 h. There was added more MeOH (60 mL) and triphenylphosphine (5.13 g, 1.2 eq.) and the mixture was stirred at room temperature for 45 min. The methanol was evaporated off, the residue was diluted with Et2O (100 mL) and the insoluble phosphine oxide filtered. The filtrate material was chromatographed on silica gel, eluting with a 1:3 mixture of ethyl acetate and hexane, to afford the compound as a colorless oil (1.25 g).

Workup

  1. customThe methanol was evaporated off
  2. additionthe residue was diluted with Et2O (100 mL)
  3. filtrationthe insoluble phosphine oxide filtered
  4. customThe filtrate material was chromatographed on silica gel
  5. washeluting with a 1:3 mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-defe7d8cff0a4cf588121389729de124
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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