反応 #8294

反応方程式

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

sodium hydride

benzyl bromide

→

title compound

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

溶媒

ethyl acetate

tetrahydrofuran

反応条件

後処理

1. 1
   温度refluxed for 3 h
2. 2
   温度The mixture is cooled
3. 3
   洗浄washed with a saturated solution of ammonium chloride (150 mL) and brine
4. 4
   乾燥The mixture is dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo

実験手順

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.

出典