3,4-dihydro-2H-pyran → HCID 12070866, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the diol 7 (6.0 g, 21.2 mmol) and dihydropyran (7.80 mL, 84.8 mmol) in CH2Cl2 (100 mL) was cooled to 0° C. A catalytic amount of p-TsOH (0.05 g, 0.26 mmol) was added and the mixture was stirred for 30 min at 0° C. The reaction was then quenched by adding sat. aqueous NaHCO3 (10 mL). Layers were separated and the aqueous phase was extracted with 2×25 mL of CH2Cl2. Combined organic layers were dried over anhydrous K2CO3, filtered and concentrated to afford a colorless oil which was purified by passage through a short column of silica (Rf =0.46, 1:1 EtOAc/hexanes). The bis-THP ether 8 (8.59 g, 89% yield) was isolated as a colorless oil which solidified upon standing. 1H NMR (CDCl3) δ (characteristic peaks only) 5.00 (m, 1H), 4.75-4.45 (m, 2H), 3.85 (m, 2H), 3.60-3.30 (m, 4H).

Provenance & Evidence