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

HRID 1512204Notes

Reaction equation

C(N(CC)CC)C.C(O)=O.[CH3:11][O:12][C:13]([C:15]1[CH:46]=[CH:45][C:18]([CH2:19][C:20]([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:36]=2)(C(OCC=C)=O)[C:21]([O:23]CC=C)=[O:22])=[CH:17][CH:16]=1)=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][O:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][CH:20]([CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:40]=2)[C:21]([OH:23])=[O:22])=[CH:45][CH:46]=1)=[O:14]

Participants

Conditions

Temperature: 110 °C

Procedure

At room temperature, a solution of 37.2 ml (267 mmol) of triethylamine and 7.6 ml (202 mmol) of formic acid in 100 ml of dioxane is added to 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. The reaction mixture is then stirred at 110° C. overnight. After the reaction has gone to completion, the reaction solution is cooled and the solvent is removed under reduced pressure. The residue obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gives 20.98 g (56.6 mmol, 70% of theory) of a colorless solid.

Workup

temperaturethe reaction solution is cooled
customthe solvent is removed under reduced pressure
customThe residue obtained
customis purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-07d9bceb64e242f39d491a06fcb7acb2
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217063B2

Reaction notes

Loading…