Sodium borohydride → (E)-2-(Phenylmethylidene)deca-3,9-diyn-1-ol

Participants

Reaction Steps

To a solution of Compound 2 (502 mg, 2.13 mmol) in methanol (20 mL) was added a solution of NaBH4 (80.4 mg, 2.13 mmol) in aqueous NaOH (0.5 N, 5 mL) followed by stirring at room temperature for 30 minutes. The reaction was then quenched with saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (50 mL×2). The combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 20 percent EtOAc in hexane) to give 462.3 mg (91.4 percent) of Compound 3: yellow oil; Rf=0.19 (17 percent EtOAc in hexane); IR (neat) 3400 (br), 3296, 2942, 2862, 2210, 2116, 1072 cm−1; 1H NMR (300 MHz, CDCl3) δ7.84-7.81 (m, 2H), 7.37-7.26 (m, 3H), 6.71 (s, 1H), 4.25 (s, 2H), 2.49 (t, J=6.65 Hz, 2H), 2.24 (td, J=6.78, 2.37 Hz, 2H), 2.17 (br s, 1H), 1.98 (t, J=2.64 Hz, 1H), 1.79-1.60 (m, 4H); 13C NMR (75 MHz, CDCl3) δ136.7, 133.3, 129.1, 128.8, 128.7, 122.5, 98.8, 84.7, 79.3, 69.3, 68.1, 28.2, 28.1, 20.0, 18.6; MS (+CI) m/z (relative intensity) 239 (M+H+, 15), 221 (100); HRMS (+EI) calcd for C17H18O 238.1358 (M+), found 238.1316.

Provenance & Evidence