Ethanol → HCID 54530068, compound

HRID 843123Notes

Reaction equation

C(O)C.[Na].[CH2:5]([O:7][C:8](=[O:23])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:12]=1[C:18]([CH:20]1[CH2:22][CH2:21]1)=O)[CH3:6]>C(OCC)(=O)C>[CH2:5]([O:7][C:8]([C:9]1[O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:12]=2[C:18]=1[CH:20]1[CH2:22][CH2:21]1)=[O:23])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To an anhydrous ethanol (2 ml) was added sodium (50 mg) at 0° C. under argon atmosphere. After 10 minutes, (2-cyclopropanecarbonyl-3-hydroxy-phenoxy)-acetic acid ethyl ester (380 mg) was added to the reaction mixture and the reaction mixture was stirred overnight at 0° C. The reaction was quenched with 2 N hydrochloric acid (5 ml) and stirred for 30 minutes yielding a white precipitate. The mixture was diluted with ethyl acetate (10 ml), washed with water (5 ml) and brine (5 ml), dried over anhydrous sodium sulfate, concentrated in vacuo. The residue was purified by silica gel column chromatography developed by hexane-ethyl acetate yielding 3-cyclopropyl-4-hydroxy-benzofuran-2-carboxylic acid ethyl ester (298 mg) as a white solid. FAB-MS: m/z 246 (M+); 1H-NMR (CDCl3): δ 0.99-1.05 (2H, m), 1.17-1.24 (2H, m), 1.45 (3H, t, J=7.26 Hz), 2.26-2.35 (1H, m), 4.45 (2H, q, J=7.26 Hz), 6.27 (1H, s), 6.71 (1H, dd, J=0.99 Hz, 8.25 Hz), 7.09 (1H, dd, J=0.99 Hz, 8.25 Hz), 6.41 (2H, d, J=8.25 Hz), 7.29 (1H, dd, J=8.25 Hz, 8.25 Hz).

Workup

customThe reaction was quenched with 2 N hydrochloric acid (5 ml)
stirringstirred for 30 minutes
customyielding a white precipitate
washwashed with water (5 ml) and brine (5 ml)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-5c42d972e1e943b8b56920720428fa1d
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376491B1

Reaction notes

Loading…