p-Toluenesulfonic acid → (E)-4,5-dimethoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one

HRID 2199833

Reaction equation

[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:14].[F:15][C:16]([F:27])([F:26])[S:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5]/[C:6](=[CH:22]\[C:21]1[CH:24]=[CH:25][C:18]([S:17][C:16]([F:27])([F:15])[F:26])=[CH:19][CH:20]=1)/[C:7]2=[O:14]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4,5-dimethoxy-2,3-dihydro-1H-inden-1-one (165) (100 mg, 0.520 mmol) in toluene 15 mL was added 4-((trifluoromethyl)thio)benzaldehyde (72) (118.4 mg, 0.572 mmol) and PTSA (178.9 mg, 1.414 mmol). The reaction was stirred at 120° C. for 6 h. The resulting reaction mixture was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 25% ethyl acetate in hexane to afford yellow coloured solid of (E)-4,5-dimethoxy-2-(4-((trifluoromethyl)thio)benzylidene)-2,3-dihydro-1H-inden-1-one intermediate 166.

Workup

customThe resulting reaction mixture
washwashed with water (3×25 mL)
dry with materialThe organic layer was dried over sodium sulphate
concentrationconcentrated
customto get the crude, which
customwas purified through flash chromatography
washThe compound was eluted at 25% ethyl acetate in hexane

Sources & evidence

ORD record: ord-d8754f6256774591989d11c928876ce9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359315B2

Linked notes

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