Pyridine → 3-[2-Methoxy-3-(methylsulfinyl)-4-(trifluoro-methyl)benzoyloxy]cyclohex-2-en-1-one

HRID 1254936Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]([S:12]([CH3:14])=[O:13])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[C:19]1(=O)[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH2:20]1.N1C=CC=CC=1.S(Cl)(Cl)=O>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[C:11]([S:12]([CH3:14])=[O:13])=[C:10]([C:15]([F:18])([F:16])[F:17])[CH:9]=[CH:8][C:4]=1[C:5]([O:7][C:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH:20]=1)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

3.0 g of 2-methoxy-3-methylsulfinyl-4-trifluoromethylbenzoic acid and 1.68 g of 1,3-cyclohexanedione are suspended in 20 ml of ethyl acetate and 5.61 ml of pyridine under an inert atmosphere and cooled to −25° C. with stirring. 1.73 g of thionyl chloride are then slowly added dropwise such that the temperature always remains below −20° C. Following the complete addition of the thionyl chloride, the mixture is stirred for a further 20 minutes. 38 μl of cold water are added, and the mixture is warmed to 0° C. 10 ml of ethyl acetate and a further 10 ml of water are then added. After separating the organic phase from the aqueous phase, the aqueous phase is extracted twice with 5 ml of ethyl acetate in each case. The combined organic phases are dried, giving 3.57 g of 3-[2-methoxy-3-(methylsulfinyl)-4-(trifluoro-methyl)benzoyloxy]cyclohex-2-en-1-one (85.5% yield).

Workup

stirringthe mixture is stirred for a further 20 minutes
customAfter separating the organic phase from the aqueous phase
extractionthe aqueous phase is extracted twice with 5 ml of ethyl acetate in each case
customThe combined organic phases are dried

Sources & evidence

ORD record: ord-f6f5e86e410c4b13855d6a37a386770b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455657B2

Reaction notes

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