Iodoethane → 5-(2,4-Diethoxy-3-methoxyphenyl)isobenzofuran-1(3H)-one

HRID 2171133Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([OH:20])[C:5]=1[O:21][CH3:22])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:29](I)[CH3:30]>C(#N)C>[CH2:29]([O:20][C:6]1[C:5]([O:21][CH3:22])=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=[CH:8][C:7]=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)[CH3:30]

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirring solution of 5-(4-ethoxy-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one (30 mg, 0.1 mmol) in acetonitrile (5 mL) was added potassium carbonate (41 mg, 0.30 mmol) and ethyl iodide (62 mg, 0.40 mmol) and the resultant reaction mixture was heated to 75° C. for 2 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 0-20% ethyl acetate in pet ether) afforded the title compound as a solid (20 mg, 61%).

Workup

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

Sources & evidence

ORD record: ord-4d1c09d14b12435da1d266cbc577d06d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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