Dichloromethane → HCID 86663825, compound

HRID 61868Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:25](=[CH:26][CH:27]=1)[CH2:24][C:8]1[C:9]3[CH:15]=[CH:14][C:13]([O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:12][C:10]=3[O:11][C:7]=1[C:6]2([CH3:29])[CH3:28].Cl([O-])=[O:31].[Na+].ON1C(=O)C2=CC=CC=C2C1=O.C(Cl)Cl>C(#N)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:31])[C:8]1[C:9]3[CH:15]=[CH:14][C:13]([O:16][S:17]([C:20]([F:21])([F:23])[F:22])(=[O:18])=[O:19])=[CH:12][C:10]=3[O:11][C:7]=1[C:6]2([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 40 °C

Procedure

Trifluoromethanesulfonic acid 8-methoxy-6,6-dimethyl-6,11-dihydro-benzo[b]naphth[2,3-d]furan-3-yl ester (Compound Z11, 4.82 g) was dissolved in acetonitrile (48 mL) and water (24 mL), added with sodium chlorite (2.55 g) and N-hydroxyphthalimide (369 mg), and then the mixture was stirred at 40° C. for 1 hr. The reaction mixture was added with methylene chloride and the organic layer was washed with saturated brine. Thereafter, the organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (2.80 g, 56%).

Workup

washthe organic layer was washed with saturated brine
dry with materialThereafter, the organic layer was dried over magnesium sulfate
customThe residues obtained
concentrationafter concentration under reduced pressure
customwere purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-7520e80c1ce94c67af2b383cbafb1dbe
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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