Triphenylphosphine → Methyl 2-ethyl-2-(1-methylethyl)-4-oxobutanoate

HRID 1108371Notes

Reaction equation

HRID 1108371 reaction equation
[CH2:1]([C:3]([CH:11]([CH3:13])[CH3:12])([CH2:8][CH:9]=C)[C:4]([O:6][CH3:7])=[O:5])[CH3:2].[O:14]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH2:1]([C:3]([CH:11]([CH3:13])[CH3:12])([CH2:8][CH:9]=[O:14])[C:4]([O:6][CH3:7])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 10607559HCID 10607559, compound

Product 1

HCID 10773902Methyl 2-ethyl-2-(1-methylethyl)-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The reaction of the olefinic ester, methyl 2-ethyl-2-(1-methylethyl)-4-pentenoate (9.20 g, 50 mmol), with ozone in CH2Cl2 (200 mL) at -78° C., followed by the treatment of the resulting ozonide with Ph3P (19.65 g, 75 mmol) as described above in the preparation of Example 7, gave 14.36 g of an oily residue. Flash chromatography over silica gel (hexanes-EtOAc, 9:1) afforded the aldehyde (8.20 g, 88%) as a colorless oil.

Workup

  1. customat -78° C.
  2. customas described above in the preparation of Example 7

Sources & evidence

ORD record
ord-ce573f0c57ca40b09c41fa27e7f27214
Source dataset
uspto-grants-2000_05
Patent number
US06066666

Reaction notes

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