Dichloromethane → HCID 86663825, compound

HRID 2275244Notes

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-f50fa3552b044efbac4125e0a1692d74
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126931B2

Reaction notes

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