Acetic Anhydride → Ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoate

HRID 1848299Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9](O)([C:25]([F:28])([F:27])[F:26])[CH2:10][C:11]([C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:24])[CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(OC(=O)C)(=O)C.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.Cl.C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:25]([F:28])([F:26])[F:27])=[CH:10][C:11]([C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:24])[CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 30 °C

Procedure

0.96 g of ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-methylbenzoate, 2.0 g of toluene, 0.43 g of acetic anhydride, 26 mg of 4-dimethylaminopyridine and 0.43 g of triethylamine were fed and the mixture was stirred for 3 hours at 30° C. 2 ml of iced water, 2 drops of concentrated hydrochloric acid and 5 ml of toluene were added to the reaction solution, and separated. The organic phase was washed with water, and the solvent was distilled off under reduced pressure to obtain 0.94 g of ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoate as a red solid.

Workup

customseparated
washThe organic phase was washed with water
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-10f1d09110fa46538bd4d6bb46288690
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952175B2

Reaction notes

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