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

HRID 854062

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-9586e1e7fd784b78b9f2afcc538bd6f7
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256204B2

Linked notes

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