Water → HCID 67824760, compound

Participants

Reaction Steps

To a -100° C. solution of 15 (200 mg, 0.46 mmol) in dry THF (8 ml) was added nBuLi (1.6M, 0.50 mmol, 0.31 ml) dropwise. The resulting black-green solution was stirred for 10 min. at which time Bu3SnCl (0.15 ml, 0.54 mmol) was added neat. The solution was allowed to reach room temperature and stirred 2 h. Water was added and the mixture was extracted with ether. The combined ether extracts were dried (MgSO4) and concentrated to a brown oil. HPLC purification of the oil (Whatman Partisil 10 column, 90:10 CH2Cl2 :EtOAc) afforded the tributylstannyl derivative 16 (150 mg, 50%). 1H NMR d (ppm): 0.85 t (CH3), 1.15-1.55 m (3 CH2), 1.49 s (3 CH3), 3.58 dd (CH2), 3.83 dd (CH2), 7.00 d (CH arom), 7.63 d (CH arom), 8.18 d (CH arom), 8.30 d (CH arom).

Provenance & Evidence