Sodium hydride → HCID 75066242, compound

Participants

Reaction Steps

A stirred solution of 203 (2.29 g, 5.72 mmol) in dry DMF (20 mL) was treated portionwise at 0° C. with NaH (275 mg, 60% in oil, 6.88 mmol). The mixture was warmed to room temperature for 30 min, then cooled to 0° C. and treated with 1,3-dichloropropene (1.66 mL, 18 mmol, mixed isomers). The mixture was stirred at room temperature for a further 6 h, then diluted with 10% aqueous NaCl and extracted with EtOAc (×2). The combined organic layers were washed with water (×2), dried, and concentrated to dryness under reduced pressure at 100° C. The residue was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (19:1) to give crude tert-butyl 1-bromo-7-(methylsulfonyl)-2-naphthyl(3-chloro-2-propen-1-yl)carbamate (204) (2.63 g, 97%) as a foam: 1H NMR [(CD3)2SO] (mixture of rotamers and B and Z forms) δ 8.78 (s, 1H), 8.32 (dd, J=8.6, 2.2 Hz, 1H), 8.18, 8.17 (2 d, J=8.7 Hz, 1H), 8.13-8.06 (1, 1H), 7.75, 7.70 (2 d, J=8.7 Hz, 1H), 6.44-6.29 (m, 1H), 6.20-6.01 (m, 1H), 4.58-4.48, 4.43-4.22, 4.16-4.05 (3 m, 21H), 3.35 (s, 3H), 1.50, 1.27 (2 s, 9H). HRMS (FAB) calcd. for C19H2279Br35ClCNO4S (m/z 474.0141, found 474.0143.

Provenance & Evidence