Sodium Hydroxide → 3-Tetrahydropyranyloxyoxetane

Participants

Reaction Steps

To 476 g of crude 3-chloro-2-tetrahydropyranyloxy-1-propyl acetate was added 216 g (5.4 moles) of sodium hydroxide in 500 mL of water. The reaction mixture was heated at reflux for 17 hours. The upper organic layer was separated and taken up in 350 mL of methylene chloride. The methylene chloride solution was dried over sodium sulfate and solvent was removed in vacuo to leave 320.9 g of 3-tetrahydropyranyloxyoxetane: 1H NMR (CDCl3) δ1.63 (br. s, 6H, CH2); 3.2-4.4 (m, 2H, --OCH2); 4.47 (br. s, 1H, CH); 4.67 (br. s, 4H, O(CH2)); 5.17 (br, s, 1H, O--CH); IR (CH2Cl2) 2970, 2910 (C--H); 980 cm-1 (oxetane). Extraction of the aqueous layer with ether gave an additional 10.3 g for an overall crude yield of 331.2 g. 3-Tetrahydropyranyloxyoxetane distilled with some decomposition at 48°-65° (0.2 mm).

Provenance & Evidence