Triphenylphosphine → HCID 10845239, compound

HRID 1955692Notes

Reaction equation

HRID 1955692 reaction equation
[CH3:1][C:2]([C:5]([CH3:13])([CH2:10][CH:11]=C)[C:6]([O:8][CH3:9])=[O:7])([CH3:4])[CH3:3].[O:14]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][C:2]([C:5]([CH3:13])([CH2:10][CH:11]=[O:14])[C:6]([O:8][CH3:9])=[O:7])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823Ozone2×HCID 10821366HCID 10821366, compound

Product 1

HCID 10845239HCID 10845239, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the olefinic ester, methyl 2-(1,1-dimethylethyl)-2-methyl-4-pentenoate (2.76 g, 15 mmol), in dry CH2Cl2 (60 mL) was reacted with ozone at -78° C. When excess ozone was observed (blue coloration), nitrogen was bubbled through the solution, and Ph3P (5.90 g, 22.5 mmol) was added in one portion while stirring. The system was allowed to warm to room temperature (ca. 2 h) and stirred for 2 more hours. The solvent was removed in vacuo and the residue triturated with hexanes (150 mL). The precipitated Ph3PO (ca. 5.78 g) was filtered off and the filtrate concentrated in vacuo to give 2.80 g of the crude product as a colorless viscous residue. Flash chromatography over silica gel (hexanes-EtOAc, 19:1) afforded 2.12 g (76%) of the aldehyde as a colorless oil.

Workup

  1. additionwas added in one portion
  2. stirringstirred for 2 more hours
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated with hexanes (150 mL)
  5. filtrationThe precipitated Ph3PO (ca. 5.78 g) was filtered off
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give 2.80 g of the crude product as a colorless viscous residue

Sources & evidence

ORD record
ord-b2ff4397f8f84d038bf3a438a78951ca
Source dataset
uspto-grants-1998_07
Patent number
US05776959

Reaction notes

Loading…