Potassium Carbonate → 5-[2,4-Dimethoxy-3-(3-methyl-oxetan-3-ylmethoxy)-phenyl]-3H-isobenzofuran-1-one

HRID 2171155Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirring solution of 5-(3-Hydroxy-2,4-dimethoxy-phenyl)-3H-isobenzofuran-1-one (80 mg, 0.279 mmol) in acetonitrile (10 mL) was added potassium carbonate (115 mg, 0.837 mmol) and 3-bromomethyl-3-methyl-oxetane (138 mg, 0.837 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 (50 mg, 48.4%).

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-b2223893d17d404fb7fb514edfc20477
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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