Formic Acid → 2-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)heptanedioic acid 7-ethyl ester

HRID 1921877Notes

Reaction equation

C([O:4][C:5]([C:7]([CH2:23][C:24]1[CH:29]=[C:28]([F:30])[C:27]([O:31][Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])=[C:26]([F:42])[CH:25]=1)([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])C(OCC=C)=O)=[O:6])C=C.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>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH:7]([CH2:23][C:24]1[CH:29]=[C:28]([F:30])[C:27]([O:31][Si:32]([CH:33]([CH3:35])[CH3:34])([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:37])[CH3:38])=[C:26]([F:42])[CH:25]=1)[C:5]([OH:6])=[O:4])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

4.2 g (6.88 mmol) of 1-allyl 7-ethyl 2-allyloxycarbonyl-2-(3,5-difluoro-4-triisopropylsilanyloxy-benzyl)heptanedioate, 39 mg (0.17 mmol) of palladium(II)acetate and 135 mg (0.52 mmol) of triphenylphosphine are stirred in 30 ml of dioxane under argon. A solution of 2.3 g (22.69 mmol) of triethylamine and 0.79 g (17.19 mmol) of formic acid in 20 ml of dioxane is then added dropwise, and the mixture is heated at 100° C. overnight. The cooled mixture is concentrated and the crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, 3:1). 2.07 g (52% of theory) of the title compound are obtained.

Workup

concentrationThe cooled mixture is concentrated
customthe crude product is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, 3:1)

Sources & evidence

ORD record: ord-ad0caec4e364464e808fc8f2c1b74963
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173704B2

Reaction notes

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