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

To a mixture of methyl 1-(spiro[benzo[d][1,3]dioxole-2,1′-cyclobutane]-5-yl)cycl-opropanecarboxylate (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).

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

ORD 기록

ord-850be82df7764639bac9867298f2f6cc

출처 데이터셋

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07776905B2