Triethylamine → Benzyl (3,4,5-trifluorophenyl)acetate

HRID 546683Notes

Reaction equation

C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[F:19][C:20]1[CH:21]=[C:22]([CH2:28]C(O)=O)[CH:23]=[C:24]([F:27])[C:25]=1[F:26].O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[F:19][C:20]1[CH:21]=[C:22]([CH2:28][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH:23]=[C:24]([F:27])[C:25]=1[F:26]

Participants

Conditions

Temperature: 0 °C

Procedure

Triethylamine (0.808 mL) and benzyl chloroformate (0.752 mL) were sequentially added dropwise to a solution of 3,4,5-trifluorophenylacetic acid (1 g) in methylene chloride (15 mL) at 0° C., and the reaction solution was stirred at 0° C. for five minutes. DMAP (64.4 mg) was added to the reaction solution which was then stirred at 0° C. for 30 minutes. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1.43 g of the title compound. The property values of the compound are as follows.

Workup

stirringwas then stirred at 0° C. for 30 minutes
customthe organic layer was separated
washThe resulting organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record: ord-0a109376805a4abd85f233325c4b350b
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935815B2

Reaction notes

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