Hydrochloric Acid → 1-(Spiro[benzo[d][1,3]-dioxole-2,1'-cyclobutane]-5-yl)cyclopropane carboxylic acid

HRID 1991671Notes

Reaction equation

[C:1]12([O:8][C:7]3[CH:9]=[CH:10][C:11]([C:13]4([C:16]([O:18]C)=[O:17])[CH2:15][CH2:14]4)=[CH:12][C:6]=3[O:5]1)[CH2:4][CH2:3][CH2:2]2.[Li+].[OH-].Cl>C1COCC1.O>[C:1]12([O:8][C:7]3[CH:9]=[CH:10][C:11]([C:13]4([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]4)=[CH:12][C:6]=3[O:5]1)[CH2:2][CH2:3][CH2:4]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of methyl 1-(spiro[benzo[d][1,3]dioxole-2,1′-cyclobutane]-5-yl)cyclopropanecarboxylate (0.60 g, 2.3 mmol) in THF/H2O (4:1, 10 mL) was added LiOH (0.30 g, 6.9 mmol). The mixture was stirred at 60° C. for 24 h. HCl (0.5 N) was added slowly to the mixture at 0° C. until pH 2-3. The mixture was extracted with EtOAc (10 mL×3). The combined organic phases were washed with brine, dried over anhydrous MgSO4, and washed with petroleum ether to give 1-(spiro[benzo[d][1,3]-dioxole-2,1′-cyclobutane]-5-yl)cyclopropane carboxylic acid (330 mg, 59%). 1HNMR (400 MHz, CDCl3) δ 6.78-6.65 (m, 3H), 2.65-2.58 (m, 4H), 1.86-1.78 (m, 2H), 1.63-1.60 (m, 2H), 1.26-1.19 (m, 2H).

Workup

extractionThe mixture was extracted with EtOAc (10 mL×3)
washThe combined organic phases were washed with brine
dry with materialdried over anhydrous MgSO4
washwashed with petroleum ether

Sources & evidence

ORD record: ord-4c10c9fa8ec24140a7dbe0d6840f1d78
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645789B2

Reaction notes

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