Sodium Hydroxide → 2-triphenylmethoxymethyl-2-propen-1-ol

Participants

Reaction Steps

To a solution of LiAlH4 (119 mg; 2.98 mmol) in dry ether (5 mL), AlCl3 (400 mg; 2.94 mmol) was added carefully at 0° C. and the mixture was stirred for 15 min. Then a solution of 12 (829 mg; 2.44 mmol) in dry ether (9 mL) was added and the reaction was stirred at 0° C. for 3 h. After that 10% aqueous NaOH (10 mL) was added to quench the reaction. The organic layer was separated and washed by saturated aqueous NaHCO3 and NaCl respectively, and dried over anhydrous K2CO3. After evaporation of the solvent, the residue was purified by flash column chromatography over silica gel using CH3OH—CH2Cl2 (1:205) as the eluent to afford 10 as colorless oil (545 mg; 65% yield): 1H NMR (400 MHz, CDCl3) δ 7.41-7.48 (m, 6H, six of ArH), 7.26-7.33 (m, 6H, six of ArH), 7.19-7.26 (m, 3H, three of ArH), 5.33 (s, 1H, one of C═CH2), 4.96 (s, 1H, one of C═CH2), 3.53 (s, 2H, Ph3COCH2), 2.70 (m, 2H, CH2CH2NH2) 2.18 (t, J=6.7 Hz, 2H, CH2CH2NH2), 2.06 (br s, 2H, NH2); 13C NMR (100 MHz, CDCl3) δ 143.6, 143.4, 128.1, 127.4, 126.5, 111.3, 86.5, 66.1, 39.8, 37.4; HRMS (FAB+) calcd for C24H26ON (M+H+): 344.2014. found: 344.2017, (11).

Provenance & Evidence