Ethyl Acetate → 3-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one

HRID 856950

Reaktionsgleichung

[OH:1][C:2]1[C:3]([C:13]#[N:14])=[CH:4][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20](=[O:23])[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[NH2:14][C:13]1[C:3]2[CH:4]=[C:5]3[C:10]([CH2:9][CH2:8][CH2:7][C:6]3=[O:12])=[CH:11][C:2]=2[O:1][C:21]=1[C:20](=[O:23])[C:19]1[CH:24]=[CH:25][CH:26]=[C:17]([O:16][CH3:15])[CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 3-hydroxy-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile from method II-6 (45 mg, 0.24 mmol) and 3-methoxyphenacyl bromide (60 mg, 0.26 mmol, 1.1 eq) in anhydrous N,N-dimethylformamide (2 mL) was added potassium carbonate (66 mg, 0.48 mmol, 2 eq). The reaction mixture was shaken at 90° C. for 17 h. The mixture was cooled to room temperature and poured into ethyl acetate and water. The aqueous layer was extracted with ethyl acetate twice. Combined the organic layers and evaporated in vacuo. The crude product was washed with methanol and gave 19 mg (24%) of 3-Amino-2-(3-methoxy-benzoyl)-7,8-dihydro-6H-naphtho[2,3-b]furan-5-one as a yellow solid. 1H-NMR (DMSO-d6) δ 8.72 (s, 1H), 7.68 to 7.42 (m, 5H), 7.18 to 7.14 (m, 1H), 6.33 (s, 1H), 3.84 (s, 3H), 3.07 (t, J=6.0 Hz, 2H), 2.65 (t, J=6.6 Hz, 2H), 2.50 (m, 2H); MS LC-MS (MH+=336.2); Rf=0.62, 50% ethyl acetate-hexane.

Aufarbeitung

temperatureThe mixture was cooled to room temperature
extractionThe aqueous layer was extracted with ethyl acetate twice
customevaporated in vacuo
washThe crude product was washed with methanol

Quellen und Nachweise

ORD-Eintrag: ord-b868b18ce04b49debaae6542a54a2db7
Quelldatensatz: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07144885B2

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