Hydrochloric Acid → 4-(4-(Difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one

HRID 2171066Notes

Reaction equation

[F:1][CH:2]([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH2:13][C:14]3=[O:19])=[C:6]([O:20]COC)[C:5]=1[O:24][CH3:25].Cl>CO>[F:1][CH:2]([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH2:13][C:14]3=[O:19])=[C:6]([OH:20])[C:5]=1[O:24][CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of 4-(4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)phenyl)-2,3-dihydro-1H-inden-1-one (1 g, 2.74 mmol) in methanol (75 mL) was added concentrated hydrochloride (5 mL) and the reaction mixture was heated to 50° C. for 1 h. The reaction mixture was cooled to RT and concentrated under reduced pressure and the obtained residue was basified with sodium bicarbonate solution and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (700 mg, 80%).

Workup

temperatureThe reaction mixture was cooled to RT
concentrationconcentrated under reduced pressure
extractionextracted with dichloromethane (3×)
washThe combined dichloromethane layers were washed with brine
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cf747b80f1c64aca8adbc6290c5d8f8e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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