Hydrochloric Acid → HCID 18790140, compound

Participants

Reaction Steps

To a suspension of 60% NaH (0.23 g, 5.84 mmol) in anhydrous DMF (15 mL) is added a solution of methyl (3,4-dimethoxyphenylsulfonyl)acetate in 20 mL of DMF (1.6 g, 5.84 mmol) dropwise over 10 minutes. The mixture is stirred at room temperature for 20 minutes. 1-Bromo-4-phenylbutane (1.6 g, 5.84 mmol) is added and the mixture is stirred at room temperature for 24 hours. The mixture is added to 5% HCl and is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed on silica gel (7:3 hexane:ethyl acetate) to afford methyl 2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanoate (1.3 g, 55%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.30-1.42 (m, 2H), 1.52-1.68 (m, 2H), 1.95-2.12 (m, 2H), 2.48-2.68 (m, 2H), 3.64 (s, 3H). 3.92 (d, 7H), 6.95 (d, 1H), 7.07-7.18 (m, 2H). 7.20-7.30 (m. 4H), 7.44 (d, 1H); MS (EI) m/e 406 (M+).

Provenance & Evidence