Hydrochloric Acid → 1-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid

HRID 401526Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl ester (1 g, 4 mmol) in MeOH (10 mL) was added LiOH (0.40 g, 9.5 mmol). The mixture was stirred at 40° C. overnight. HCl (10%) was added slowly to adjust the pH to 5. The resulting mixture was extracted with ethyl acetate (10 mL×3). The extracts were washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the crude product was purified by preparative HPLC to give 1-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid (0.37 g, 41%). 1H NMR (400 MHz, CDCl3) δ 7.11-7.07 (m, 2H), 6.71 (d, J=8 Hz, 1H), 4.23 (s, 2H), 1.66-1.63 (m, 2H), 1.32 (s, 6H), 1.26-1.23 (m, 2H).

Workup

extractionThe resulting mixture was extracted with ethyl acetate (10 mL×3)
washThe extracts were washed with brine
dry with materialdried over Na2SO4
customThe solvent was removed under vacuum
customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-6760410ca1bf4464a134a378237e6106
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741933B2

Reaction notes

Loading…