Acetate → HCID 13676003, compound

HRID 1646101Notes

Reaction equation

HRID 1646101 reaction equation
[C:1]1([CH:6]=O)[CH2:5][CH2:4][CH2:3][CH:2]=1.[C:8]([O-:11])(=[O:10])[CH3:9].[CH:12]1C=CC=CC=1>>[C:1]1(/[CH:6]=[CH:9]/[C:8]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 3

HCID 175AcetateHCID 241BenzeneHCID 1386721-Cyclopentene-1-carboxaldehyde

Product 1

HCID 13676003HCID 13676003, compound

Procedure

1-cyclopentene-1-carboxaldehyde (9.60 g, 100 mmoles) was mixed with methyl (triphenylphosphoraylidene) acetate (40.1 g, 120 mmoles) in 80 ml of benzene and was brought to reflux under nitrogen for 5 hours. After cooling, the solids were filtered off, washed with ether and discarded. The solvent mixture was concentrated in vacuo, triturated with several volumes of pentane, filtered and stripped. Flash chromatography on silica gel afforded 14.8 g of the desired ester as a pure, white solid.

Workup

  1. temperatureto reflux under nitrogen for 5 hours
  2. temperatureAfter cooling
  3. filtrationthe solids were filtered off
  4. washwashed with ether
  5. concentrationThe solvent mixture was concentrated in vacuo
  6. customtriturated with several volumes of pentane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-1b7c37883f6d41b1a3dc3aff0be7411e
Source dataset
uspto-grants-1993_01
Patent number
US05177251

Reaction notes

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