Methanol → HCID 14579798, compound

HRID 1607282Notes

Reaction equation

[CH2:1]([C:8]1[O:9][C:10]2[CH:17]=[C:16]3[O:18]C[O:20][C:15]3=[CH:14][C:11]=2[C:12]=1[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[CH2:1]([C:8]1[O:9][C:10]2[CH:17]=[C:16]([OH:18])[C:15]([OH:20])=[CH:14][C:11]=2[C:12]=1[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -25 °C

Procedure

A solution of 2-benzyl-3-methyl-5,6-methylenedioxybenzofuran (226 mg, 0.85 mmole) in methylene chloride (10 mL) was cooled at -65° C. and a 1M solution of boron tribromide in methylene chloride (0.85 mL) was added dropwise. The mixture was allowed to warm up to -25° C. and was kept in that range for 1 hour. Methanol (5 mL) was then added and the mixture was evaporated in vacuo. The residue was chromatographed on silica gel and eluted with 25% ethylacetate in hexane to yield 128 mg of 2-benzyl-3-methyl-5,6-dihydroxybenzofuran, mp. 95.5°-98° C.

Workup

customthe mixture was evaporated in vacuo
customThe residue was chromatographed on silica gel
washeluted with 25% ethylacetate in hexane

Sources & evidence

ORD record: ord-4db3dee092e04a3b9870625347e7f269
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863958

Reaction notes

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