Sodium hydride → (+)-6-(2-Benzofuranyl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin

HRID 1166554Notes

Reaction equation

[CH3:1][N:2]([CH2:4][CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH2:7]1)[CH3:3].[H-].[Na+].Cl[CH2:20][C:21]1[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[CH:25]=1>CN(C=O)C.C1COCC1.O>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[CH:25]=[C:21]1[CH2:20][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])[CH2:15][CH2:14]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (+)-2-[2-(N,N-dimethylamino) ethyl]-6-hydroxytetralin (0.217 g) in DMF (5 ml) was added sodium hydride (60% in oil, 0.052 g) at room temperature. The reaction mixture was stirred at 50° C. for one hr and cooled to 0° C. A solution of 2-chloromethylbenzofuran (0.187 g) in THF (5 ml) was added to the solution. The reaction mixture was stirred at 0° C. for one hr, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:4) and recrystallized from ethyl acetate-hexane to obtain the titled compound (17 mg).

Workup

temperaturecooled to 0° C
stirringThe reaction mixture was stirred at 0° C. for one hr
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated aqueous sodium chloride
customdried
concentrationconcentrated
customThe residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:4)
customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-53681be9a12f4dc9b94da3f388942bc8
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613805B2

Reaction notes

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