Trifluoroacetic acid → 3-(4-(Methoxycarbonyl)phenyl)-2-methylenebutanoic acid

HRID 931396Notes

Reaction equation

FC(F)(F)C(O)=O.C([O:12][C:13]([C:15](=[CH2:28])[CH:16]([C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[CH3:17])=[O:14])(C)(C)C>ClCCl>[CH3:25][O:24][C:22]([C:21]1[CH:26]=[CH:27][C:18]([CH:16]([CH3:17])[C:15](=[CH2:28])[C:13]([OH:14])=[O:12])=[CH:19][CH:20]=1)=[O:23]

Participants

Conditions

Temperature: 23 °C

Procedure

Trifluoroacetic acid (21.7 mL, 283 mmol) was added to a solution of methyl 4-(3-(tert-butoxycarbonyl)but-3-en-2-yl)benzoate (8.7 g, 30 mmol) in anhydrous dichloromethane (85 mL), and the mixture was stirred at 23° C. for 5 h. The solvents were removed under reduced pressure and the residue was triturated with hexane. The solid was collected by filtration and dried under vacuo to give the title compound. MS: m/z=233.0 (M+1).

Workup

customThe solvents were removed under reduced pressure
customthe residue was triturated with hexane
filtrationThe solid was collected by filtration
customdried under vacuo

Sources & evidence

ORD record: ord-131fafe1dd9e48a18aa3f7caf9d1de20
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296750B2

Reaction notes

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