Water → 7-methylspiro[2H-benzofuran-3,1-cyclopropane]-4-ol

HRID 527617Notes

Reaction equation

HRID 527617 reaction equation
COC[O:4][C:5]1[C:10]2[C:11]3([CH2:14][O:15][C:9]=2[C:8]([CH3:16])=[CH:7][CH:6]=1)[CH2:13][CH2:12]3.O>C(O)C.Cl>[CH3:16][C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[C:10]2[C:11]3([CH2:13][CH2:12]3)[CH2:14][O:15][C:9]=12

Participants

5

Reactant 2

HCID 962WaterHCID 679599444-(Methoxymethoxy)-7-methyl-2H-spiro[benzofuran-3,1'-cyclopropane]2×

Product 1

HCID 574113017-methylspiro[2H-benzofuran-3,1-cyclopropane]-4-olYield 80.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 4-(methoxymethoxy)-7-methyl-spiro[2H-benzofuran-3,1′-cyclopropane] (Intermediate 155, 38 mg, 0.17 mmol) in ethanol (5 ml), HCl 6N in water (0.1 mL, 0.6 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. Combined solvents were removed under reduced pressure and 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 (24 mg) as a light orange solid.

Workup

  1. customCombined solvents were removed under reduced pressure
  2. 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-e8c1a357327a4cc0ae5ccd9bc5f2884a
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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