Sodium Thiosulfate → HCID 11736972, compound

Participants

Reaction Steps

To a room temperature solution of (E)-3-[tris-(1-methylethyl)silyloxy]but-2-en-1-ol (crude from the previous step, assumed 17.6 mmol) in dichloromethane (100 mL) was added Dess-Martin periodinane (9.7 g, 22.9 mmol). The resulting suspension was stirred for 60 minutes, until the reaction was judged to be complete by TLC. The reaction mixture was diluted with Et2O and a saturated aqueous solution of NaHCO3 containing Na2S2O3 was added. This mixture was stirred vigorously until both layers became clear. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (5% Et2O/pentane) to afford the title compound as a colorless oil (3.69 g, 82% yield). IR (film) 2944, 2867, 1681, 1464, 1384, 1123 cm−1; 1H NMR (300 MHz, CDCl3) δ 10.09 (d, 1H, J=8.3 Hz, CHO), 6.28 (dd, 1H, J=1.5, 8.4 Hz, CH), 4.28 (d, 2H, J=0.9 Hz, CH2OTIPS), 2.09 (d, 3H, J=0.6 Hz, CH3C), 1.1 to 1.0 (m, 21H, TIPSO); 13C NMR 75 MHz, CDCl3) δ 191.2, 161.6, 124.1, 67.0, 18.0, 14.1, 11.9; HRMS (EI+) exact mass calculated for [M]+(C14H28O2Si) requires m/z 256.1859, found m/z 256.1862.

Provenance & Evidence