Sodium hydride → HCID 69135032, compound

Participants

Reaction Conditions

Reaction Steps

Tetrahydropyran-4-ol (19.72 g; 0.193 mol) was added dropwise (rapid addition) to a suspension of sodium hydride (8.5 g; 0.213 mol) in DMF (200 ml) under argon. The mixture was heated at 50° C. for 40 minutes then cooled to ambient temperature. 2-tert-Butoxyethyl bromide (35 g, 0.193 mol), (J. Med. Chem. 1966, 361), was added dropwise followed by sodium iodide (approximately 1 g) and 15-crown-5 (20 drops). The mixture was heated at 105° C. for 1 hour. Upon cooling to ambient temperature the mixture was poured into a saturated solution of ammonium chloride and extracted with ether (2×1 l). The organic phase was washed with water, brine, dried (MgSO4) and the solvent evaporated off to give 4-(2-tert-butoxyethoxy)tetrahydropyran (25 g, 64%) as a light brown oil.

Provenance & Evidence