Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate → Phenylmethyl 4-(2,3-dihydro-1H-inden-2-yl)-2-butenoate

HRID 1289441Notes

Reaction equation

HRID 1289441 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][CH:11]=O.[CH2:13]([O:20][C:21]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([O:20][C:21](=[O:22])[CH:23]=[CH:11][CH2:10][CH:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetateHCID 113786562-(2,3-dihydro-1H-inden-2-yl)acetaldehyde

Product 1

HCID 54078263Phenylmethyl 4-(2,3-dihydro-1H-inden-2-yl)-2-butenoateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved in 50 ml of methylene chloride were 3.97 g (24.8 mmol) of (indan-2-yl)acetaldehyde, and 12.2 g (29.8 mmol) of benzyloxycarbonylmethylene triphenylphosphorane were added to the solution, followed by stirring for 1.5 hours. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:20) to obtain 6.45 g of a colorless oily substance. Yield: 89%.

Workup

  1. additionwere added to the solution
  2. distillationAfter the solvent was distilled off
  3. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:20)
  4. customto obtain 6.45 g of a colorless oily substance

Sources & evidence

ORD record
ord-f8b2ab533da2487397354744c93ace2e
Source dataset
uspto-grants-1998_05
Patent number
US05750524

Reaction notes

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