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

HRID 2372993

Reaktionsgleichung

Reaktionsgleichung von HRID 2372993
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007857Zinc OxideKatalysatorHCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fcdf50ea001d41dbac6abbab76a4e9e1
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05101048

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