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

HRID 1654942Notes

Reaction equation

HRID 1654942 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

3.97 g (24.8 mmol) of (indan-2-yl)acetaldehyde was dissolved in 50 ml of methylene chloride, to which was added 12.2 g (29.8 mmol) of benzyloxycarbonylmethylene triphenyl phosphorane and stirred for 1.5 hours. The solvent was distilled off and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 6.45 g colorless oil. Yield: 89%

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-026a85903f144b8ea3c33dd98668d38f
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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