Potassium Carbonate → 4-[4-Difluoromethoxy-3-methoxy-2-(3-methoxy-2,2-dimethyl-propoxy)-phenyl]-indan-1-one

HRID 2171071Notes

Reaction equation

[F:1][CH:2]([F:23])[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:21][CH3:22].[C:24](=[O:27])([O-])[O-].[K+].[K+].Br[CH2:31][C:32]1([CH3:36])[CH2:35]O[CH2:33]1>C(#N)C>[F:1][CH:2]([F:23])[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][CH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][O:27][CH3:24])[C:5]=1[O:21][CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring solution of 4-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one (75 mg, 0.234 mmol) in acetonitrile (10 mL) was added potassium carbonate (96.8 mg, 0.702 mmol) and 3-bromomethyl-3-methyl-oxetane (115 mg, 0.702 mmol) and the resultant reaction mixture was heated to 80° C. for 16 h. The reaction mixture was cooled to RT and filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 0-20% ethyl acetate in pet ether) to afford title compound as a solid (25 mg, 26%).

Workup

customthe resultant reaction mixture
temperatureThe reaction mixture was cooled to RT
filtrationfiltered through celite
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by column chromatography (silica gel, 0-20% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-ffd51962f69c4db99394440b58324dc9
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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