1-Bromo-2-methylpropane → 4(3-Isobutoxy-2,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

HRID 2171144Notes

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+].[CH2:28](Br)[CH:29]([CH3:31])[CH3:30]>C(#N)C>[CH2:28]([O: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])[CH:29]([CH3:31])[CH3:30]

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 (10 mL) was added potassium carbonate (115 mg, 0.843 mmol) and isobutyl bromide (115 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 (15 mg, 15.7%).

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-f00a80470d0c45e0a0ad4f7e8f533872
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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