(Ethoxycarbonylmethyl)triphenylphosphonium bromide → (5-Methylbenzofuran-2-yl)acetic acid ethyl ester

HRID 481411

Reaction equation

HRID 481411 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=O)[CH2:7][C:6]=2[CH:11]=1.[Br-].[C:13]([CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C(C)=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[CH2:18][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:11][C:6]=2[CH:7]=1)[CH3:17]

Participants

4

Reactant 2

HCID 73731(Ethoxycarbonylmethyl)triphenylphosphonium bromideHCID 100576465-methyl-3H-benzofuran-2-one2×

Product 1

HCID 70085569(5-Methylbenzofuran-2-yl)acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of the product of Step 2, above (56) (10.81 mmol) and (carbethoxymethyl)triphenylphosphonium bromide (12.0 mmol) in 50 ml of xylene was heated to 155° C. for 20 hours. The reaction was cooled to ambient temperature and concentrated to dryness. The crude residue was chromatographed on silica gel with gradient elution with 5% EtOAc in hexanes to 10% EtOAc in hexanes to obtain the title compound (57).

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude residue was chromatographed on silica gel with gradient elution with 5% EtOAc in hexanes to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-c08257b8fabf46059237a9ce479172fe
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Linked notes

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