Potassium Carbonate → 4-(3-((3-(Hydroxymethyl)oxetan-3-yl)methoxy)-2,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

HRID 2171147Notes

Reaction equation

[OH:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH2:13][C:14]3=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]1([CH2:34][OH:35])[CH2:33][O:32][CH2:31]1>C(#N)C>[OH:35][CH2:34][C:30]1([CH2:29][O:1][C:2]2[C:3]([O:20][CH3:21])=[C:4]([C:10]3[CH:18]=[CH:17][CH:16]=[C:15]4[C:11]=3[CH2:12][CH2:13][C:14]4=[O:19])[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])[CH2:33][O:32][CH2:31]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring solution of 4-(3-hydroxy-2,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one (80 mg, 0.281 mmol) in acetonitrile (5 mL) was added potassium carbonate (115 mg, 0.843 mmol) and (3-(bromomethyl)oxetan-3-yl)methanol (153 mg, 0.843 mmol) and the resultant reaction mixture was heated to 80° C. for 4 h. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, 0-50% ethyl acetate in pet ether) to afford the title compound as a solid (30 mg, 27.6%).

Workup

customthe resultant reaction mixture
filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by column chromatography (silica gel, 0-50% ethyl acetate in pet ether)

Sources & evidence

ORD record: ord-26c5d813eb4c4ed2aba7390c9016c43b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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