(E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-ol → (E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-al

Participants

Reaction Steps

To a solution of Compound 4 (399.4 mg, 1.10 mmol) in dry CH2Cl2 (50 mL) cooled at 0° C. in an ice-water bath was added PCC (591.3 mg, 2.74 mmol) followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with Et2O and filtered through a short silica gel plug with rinsing by EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 17 percent EtOAc in hexane) to give 296.6 mg (75 percent) of Compound 5: pale yellow oil; Rf=0.36 (17 percent EtOAc in hexane); IR (neat) 2942, 2230, 1690, 1596, 1450, 1324, 1180 cm−1; 1H NMR (300 MHz, CDCl3) δ9.55 (s, 1H), 8.10-8.04 (m, 2H), 7.48-7.44 (m, 3H), 7.42 (s, 1H), 2.60 (td, J=6.66, 2.46 Hz, 2H), 2.44 (t, J=6.75, 2H), 1.83-1.66 (m, 4H); 13C NMR (75 MHz, CDCl3) δ192.4, 151.9, 134.8, 132.1, 131.0, 129.4, 124.0, 103.3, 94.7, 75.4, 28.3, 28.0, 21.1, 20.3, −5.9; MS (+CI) m/z (relative intensity) 363 (M+H+, 40), 207 (100); HRMS (+EI) calcd for C17H15IO 362.0168 (M+), found 362.0107.

Provenance & Evidence