4-Cyanophenol → 4-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 2372993

반응식

HRID 2372993 반응식
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][CH:6]1Br)(=[O:3])[CH3:2].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(#N)C.[O-2].[Zn+2]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 2

HCID 130194-CyanophenolHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

생성물 1

HCID 150678464-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside수율 35%

시약·촉매·용매 3

HCID 3007857Zinc Oxide촉매HCID 1140Toluene용매HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

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.

후처리

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

출처 및 근거

ORD 기록
ord-fcdf50ea001d41dbac6abbab76a4e9e1
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05101048

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