반응 #6125

반응 방정식

2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide

4-hydroxybenzonitrile

→

expected product

수율 35.0%

4-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside

수율 35.0%

용매

toluene

acetonitrile

반응 조건

후처리

1. 1
   여과The reaction medium is subsequently filtered on Celite® in ethyl acetate
2. 2
   세척washed with a 1N aqueous solution of hydrochloric acid, water
3. 3
   기타The solution obtained
4. 4
   건조is dried over sodium sulfate
5. 5
   기타the solvent is evaporated off under reduced pressure
6. 6
   기타The residue obtained
7. 7
   기타is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent

실험 절차

A suspension of 0.5 g (1.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 0.25 g (2.1.10-3 mol) of 4-hydroxybenzonitrile and 170 mg (2.1.10-3 mol) of zinc oxide (ZnO) in 4 ml of anhydrous toluene and 4 ml of acetonitrile is stirred at 50° C., under an inert atmosphere, in the presence of a molecular sieve (1 nm), for 48 h. The reaction medium is subsequently filtered on Celite® in ethyl acetate and then washed with a 1N aqueous solution of hydrochloric acid, water, a 1N solution of sodium hydroxide and then a saturated solution of NaCl. The solution obtained is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue obtained is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent to give 194 mg (yield: 35%) of the expected product.

출처