Dichloromethane → HCID 12463469, compound

HRID 1178561Notes

Reaction equation

HRID 1178561 reaction equation
[CH:1](=O)[CH2:2][CH2:3]CC.[C:7]([CH2:12][CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:9][CH2:10][CH3:11])=[O:8].[CH2:33](Cl)Cl>>[CH3:33]/[C:12](=[CH:13]\[CH2:1][CH2:2][CH3:3])/[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8063PentanalHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 12463469HCID 12463469, compoundYield 85%

Procedure

Valeraldehyde (2.5 g, 29.02 mmol) and (carbethoxyethylidene)triphenyl phosphorane (12.54 g, 34.83 mmol) in methylene chloride was refluxed for 7 hours. After cooling to room temperature, the solvent was evaporated. The residue was purified through flash chromatography on silica gel (EtOAc:Hexanes=2:98) to give 4.2 g as colorless oil in 85% yield. 1HNMR (CD3Cl): δ 0.920 (t, J=7.4 Hz, 3H), 1.30 (m, 7H), 1.81 (s, 3H), 2.19 (t, J=7.4 Hz, 2H), 4.18 (q, J=7.4 Hz, 2H), 6.75 (t, J=7.4 Hz, 1H).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified through flash chromatography on silica gel (EtOAc:Hexanes=2:98)
  3. customto give 4.2 g as colorless oil in 85% yield

Sources & evidence

ORD record
ord-35f9044fad5f4c6e816996fbd9c7456b
Source dataset
uspto-grants-2007_10
Patent number
US07276531B2

Reaction notes

Loading…