Formic Acid → 2-[4-(Methoxycarbonyl)benzyl]-4-[4-(methoxycarbonyl)phenyl]butanoic acid

HRID 1913791Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:36]=[CH:35][C:8]([CH2:9][C:10]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=2)(C(OCC=C)=O)[C:11]([O:13]CC=C)=[O:12])=[CH:7][CH:6]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(O)=O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]([CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:30]=2)[C:11]([OH:13])=[O:12])=[CH:35][CH:36]=1)=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 40 g (80.9 mmol) of diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate, 1.49 g (5.67 mmol) of triphenylphosphine and 363 mg of palladium acetate in 500 ml of dioxane is mixed at room temperature with a solution of 37.2 ml (267 mmol) of triethylamine and 7.6 ml (202 mmol) of formic acid in 100 ml of dioxane. The reaction mixture is then stirred at 110° C. overnight. After conversion is complete, the reaction solution is cooled, and the solvent is removed in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). 20.98 g (56.6 mmol, 70% of theory) of a colourless solid are obtained.

Workup

temperaturethe reaction solution is cooled
customthe solvent is removed in vacuo
customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)
custom20.98 g (56.6 mmol, 70% of theory) of a colourless solid are obtained

Sources & evidence

ORD record: ord-6c24535f961a455a82f4500355dd926a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609727B2

Reaction notes

Loading…