Toluene → Ethyl 2-(benzofuran-3-yl)acetate

HRID 222458

Reaction equation

HRID 222458 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3](=O)[CH2:2]1.[C:11]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:13])=[O:12].[C:34]1(C)C=CC=C[CH:35]=1>>[CH2:34]([O:13][C:11](=[O:12])[CH2:14][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][CH:2]=1)[CH3:35]

Participants

4

Reactant 3

HCID 1140TolueneHCID 23556CoumaranoneHCID 10870911Carboxymethylene triphenylphosphorane

Product 1

HCID 7537531Ethyl 2-(benzofuran-3-yl)acetateYield 58%

Procedure

To a solution of benzofuran-3-one (1.00 g, 7.45 mmol) in toluene (25 mL) was added (carboxymethylene)triphenyl phosphorane (3.92 g, 11.2 mmol), and the mixture was refluxed for 24 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified by column chromatography (hexane, then ethyl acetate:hexane; 1:3) to give a product (0.89 g, 58%). The spectral data for this compound are identical to that reported in the literature. (Deshpande, A. R.; Paradkar, M. V. Syn.Commun., 1990, 20, 809).

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (hexane

Sources & evidence

ORD record
ord-1513cc8125f34864afdb3594f4dce104
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Linked notes

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