Toluene → 4-Chloro-2-(5-isoxazolyl)-5-methylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907069Notes

Reaction equation

HRID 907069 reaction equation
[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]1Br)(=[O:3])[CH3:2].[Cl:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]([OH:28])=[C:23]([C:29]2[O:33][N:32]=[CH:31][CH:30]=2)[CH:22]=1.C1(C)C=CC=CC=1>[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+].C(#N)C>[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:28][C:24]1[CH:25]=[C:26]([CH3:27])[C:21]([Cl:20])=[CH:22][C:23]=1[C:29]1[O:33][N:32]=[CH:31][CH:30]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 1140TolueneHCID 8540424-Chloro-2-(5-isoxazolyl)-5-methylphenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 248312314-Chloro-2-(5-isoxazolyl)-5-methylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 10%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 10931941Silver imidazolateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.8 g (5.87 mmol) of zinc chloride, 2 g of 13× molecular sieve, 2 g (5.6 mmol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1 g (4.77 mmol) of 4-chloro-2-(5-isoxazolyl)-5-methylphenol, 1 g (5.7 mmol) of silver imidazolate, 5 ml of toluene and 5 ml of acetonitrile is prepared. The mixture is kept stirred at 80° C. for 90 minutes and then cooled and filtered. The residual solid is rinsed on the filter with methanol and the combined filtrates are concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel, elution being carried out using a dichloromethane/ethyl acetate mixture (9/1; v/v). The pure fraction is crystallized from ethyl ether. The expected compound is thus obtained in the form of a white solid with a yield of 10%.

Workup

  1. customis prepared
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe residual solid is rinsed on the
  5. filtrationfilter with methanol
  6. concentrationthe combined filtrates are concentrated under reduced pressure
  7. customThe crude product obtained
  8. customis purified by chromatography on silica gel, elution
  9. customThe pure fraction is crystallized from ethyl ether

Sources & evidence

ORD record
ord-11ee1b2f8c374600a95f8a22fe0cc99f
Source dataset
uspto-grants-2011_09
Patent number
US08013010B2

Reaction notes

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