반응 #48111

ord-048665e75f7845788f889966428dc5d0

반응 방정식

COCCBr
2-Bromoethyl methyl ether
N#Cc1ccc([C@@]2(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1Cc1ccc(O)cc1
4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzonitrile
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
O
water
COCCOc1ccc(Cc2cc([C@@]3(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2C#N)cc1
4-(β-D-glucopyranos-1-yl)-2-(4-methoxyethoxy-benzyl)-benzonitrile

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONare added
  2. 2
    추출The resulting mixture is extracted with ethyl acetate
  3. 3
    건조the combined extracts are dried over sodium sulphate
  4. 4
    기타the solvent is removed under reduced pressure
  5. 5
    기타The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

실험 절차

2-Bromoethyl methyl ether (85 μl) is added to a mixture of 4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzonitrile (0.30 g) and cesium carbonate (0.39 g) in 3 mL of dimethylformamide. The mixture is stirred at 80° C. for 16 h, before water and brine are added. The resulting mixture is extracted with ethyl acetate, the combined extracts are dried over sodium sulphate and the solvent is removed under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07745414B2uspto-grants-2010_06