Triethylamine → Ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-methylbenzoate

HRID 1848287Notes

Reaction equation

[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:15])[CH:5]=1)(=[O:3])[CH3:2].[Cl:16][C:17]1[CH:18]=[C:19]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1.C(N(CC)CC)C>CCCCCCC>[Cl:16][C:17]1[CH:18]=[C:19]([C:24]([OH:29])([C:25]([F:26])([F:27])[F:28])[CH2:2][C:1]([C:4]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:15])[CH:5]=2)=[O:3])[CH:20]=[C:21]([Cl:23])[CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.63 g of ethyl 4-acetyl-2-methylbenzoate, 0.73 g of 3′,5′-dichloro-2,2,2-trifluoroacetophenone, 0.73 g of n-heptane and 0.30 g of triethylamine were fed and the mixture was stirred for 4 hours at 60° C. The mixture was left to cool, and further stirred for one night at room temperature. 0.53 g of n-heptane was added to the slurry-state reaction solution, and the mixture was filtered under reduced pressure. The solid was washed with a small amount of n-heptane, and dried under reduced pressure. 0.97 g of ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-methylbenzoate as a light yellow solid was obtained by drying under reduced pressure.

Workup

waitThe mixture was left
temperatureto cool
stirringfurther stirred for one night at room temperature
filtrationthe mixture was filtered under reduced pressure
washThe solid was washed with a small amount of n-heptane
customdried under reduced pressure

Sources & evidence

ORD record: ord-08331cd078344a07881aafdb4cadc1a1
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952175B2

Reaction notes

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