Diethyl Ether → 8-(4-Styryl-benzyloxy)-naphthalene-1-carboxylic acid dimethylamide

Reaction equation

[H-].[Na+].Cl[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.CC[O:21][CH2:22][CH3:23].[CH3:24][N:25]([CH:27]=[O:28])[CH3:26]>>[CH3:24][N:25]([CH3:26])[C:27]([C:9]1[C:23]2[C:7](=[CH:8][CH:11]=[CH:12][C:22]=2[O:21][CH2:4][C:5]2[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=2)[CH:6]=[CH:5][CH:10]=1)=[O:28]

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 6228Dimethylformamide

HCID 24758Sodium hydride2×

HCID 35309884-Chloromethylstilbene

Product 1

HCID 538577968-(4-Styryl-benzyloxy)-naphthalene-1-carboxylic acid dimethylamide

Procedure

To a solution of 8-hydroxynaphthalene-1-(N,N-dimethyl)carboxamide (100 mg, 0.46 mmol) in dry DMF (4 mL) was added sodium hydride (12 mg, 0.51 mmol, 1.1 eq). The sodium hydride was added as 20 mg of a 60% dispersion in mineral oil that had been previously washed with 3×heptane portions under an inert atmosphere. The mixture was stirred for 30 minutes at room temperature, and 4-chloromethylstilbene (117 mg, 0.51 mmol, 1.1 eq) was added. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured onto ice/water (100 mL) and the aqueous-DMF layer was extracted into ethyl acetate portions. The combined organic layers were washed (brine), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, eluant:ethyl acetate/heptane mixtures) to give the desired ether (yield: 108 mg, 0.27 mmol, 58%);