2,5-Dimethoxytetrahydrofuran → HCID 14521576, compound

Participants

Reaction Steps

To 2,5-dimethoxytetrahydrofuran (39.6 g, 0.3 mol) in CH2Cl2 (anhydrous, 200 mL) at -78° C. under nitrogen was added TiCl4 (66 mL, 0.6 mol). After stirring for 30 min, 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene, 2, (78 g, 0.3 mol) in CH2Cl2 (anhydrous, 400 mL) was added at a rate such that the internal temperature was maintained below -55° C. The mixture was stirred for 3 h. Saturated NaHCO3 was added until the mixture was neutral to pH paper. The aqueous layer was extracted with ether (3×1 L). The dried (MgSO4) combined organic layers were concentrated to dryness. The residue was purified by flash chromatography (20% EtOAc/hexanes) to afford 20.5 g (37%) of 3 as a light brown oil.

Provenance & Evidence