p-Toluenesulfonic acid → (E)-2-(5-chloro-2-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

HRID 62243

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:28]([F:31])([F:30])[F:29])=[C:24]([CH:27]=1)[CH:25]=O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:28]([F:29])([F:30])[F:31])=[C:24]([CH:27]=1)/[CH:25]=[C:8]1/[C:9](=[O:12])[C:10]2[C:6]([CH2:7]/1)=[CH:5][C:4]([N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)=[C:3]([O:2][CH3:1])[CH:11]=2

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of 13 (100 mg, 0404 mmol) in toluene 5 mL was added 5-chloro-2-(trifluoromethyl)benzaldehyde 51 (84.4 mg, 0.404 mmol) and PTSA (153.9 mg, 0.809 mmol). The reaction was stirred at 120° C. for 6 h. The 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 compound 52. The crude 52 was purified through flash chromatography by using 100-200 mesh silica gel. The compound (E)-2-(5-chloro-2-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 52 was eluted at 28% ethyl acetate in hexane to afford yellow coloured solid.

Aufarbeitung

washwashed with water (3×25 mL)
dry with materialThe organic layer was dried over sodium sulphate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-62d4719d80604e709b80dd79588b42f4
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09446047B2

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