Water → 2H-Spiro[benzofuran-3,1'-cyclopropan]-4-ol

HRID 1505439Notes

Reaction equation

COC[O:4][C:5]1[C:10]2[C:11]3([CH2:14][O:15][C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH2:13][CH2:12]3.O>CO.Cl>[C:11]12([C:10]3=[C:5]([OH:4])[CH:6]=[CH:7][CH:8]=[C:9]3[O:15][CH2:14]1)[CH2:13][CH2:12]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-{[(methyloxy)methyl]oxy}spiro[1-benzofuran-3,1′-cyclopropane] (Reference Intermediate 213, 118 mg) in methanol (5 ml), HCl 2N in water (0.286 mL, 0.572 mmol) was added and the reaction mixture was stirred overnight at 50° C. Combined solvents were removed under reduced pressure and the residue was re-dissolved in toluen (10 ml) and the solvent was removed. The residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 7:3 as eluents affording the title compound as a white solid (70 mg).

Workup

customCombined solvents were removed under reduced pressure
dissolutionthe residue was re-dissolved in toluen (10 ml)
customthe solvent was removed
customThe residue was purified by flash chromatography (Biotage system) on silica gel using a 10 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 7:3 as eluents

Sources & evidence

ORD record: ord-b3c7059333be4f89b49e631be5956cb1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216967B2

Reaction notes

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