반응 #8294

반응 방정식

(R)-5-hydroxymethyl-dihydro-furan-2-one

sodium hydride

benzyl bromide

→

title compound

(R)-5-Benzyloxymethyl-dihydro-furan-2-one

용매

ethyl acetate

tetrahydrofuran

반응 조건

후처리

1. 1
   온도refluxed for 3 h
2. 2
   온도The mixture is cooled
3. 3
   세척washed with a saturated solution of ammonium chloride (150 mL) and brine
4. 4
   건조The mixture is dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo

실험 절차

To a solution of (R)-5-hydroxymethyl-dihydro-furan-2-one (5 g, 43.06 mmol) in tetrahydrofuran (130 mL) is added sodium hydride (2.58 g, 60% oil dispersion, 64.59 mmol) and tetrabutylammonium iodide (spatula) and stirred for 30 min. To the mixture is added benzyl bromide (6.18 mL, 51.67 mmol) and refluxed for 3 h. The mixture is cooled and diluted with ethyl acetate (150 mL), washed with a saturated solution of ammonium chloride (150 mL) and brine. The mixture is dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound, 8.87 g (100%), as a pale yellow oil.

출처