(Diethylamino)sulfur trifluoride → HCID 54250429, compound

Participants

Reaction Steps

To a -78° C. solution of Diethylaminosulfur trifluoride (DAST) (0.06 ml, 0.42 mmol) in dry CH2C2 was slowly added a solution of 13 (50 mg, 0.14 mmol) in dry CH2C2 (3 ml). The solution was allowed to warm to room temperature and stirred for 1 h. Saturated aqueous NaHCO3 was added and the mixture was extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. The residue was purified by HPLC (Whatman Partisil M9 column, 90:10 CH2Cl2 :EtOAc) to afford the fluoroethyl derivative 14 (33 mg, 66%). 1H NMR d (ppm): 1.48 s (3 CH3), 3.36 dt (CH2), 3.56 dd (NCH2), 3.71 dd (NCH2), 4.69 dt (CH2), 6.99 d (CH arom), 7.11 d (CH arom), 7.46 dd (CH arom), 7.61 d (CH arom), 8.10 d (CH arom).

Provenance & Evidence