Toluene → 2-acetyl-7-benzofuranyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 1993720

Reaction equation

HRID 1993720 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].C1(C)C=CC=CC=1.[C:21]([O:24][C@@H:25]1[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:28][S:27][CH:26]1Br)(=[O:23])[CH3:22].[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C(N(CC)CC)C.C(#N)C>[C:21]([O:24][C@@H:25]1[C@@H:30]([O:31][C:32](=[O:34])[CH3:33])[C@H:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:28][S:27][C@H:26]1[O:13][C:12]1[C:6]2[O:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:8][C:7]=2[CH:9]=[CH:10][CH:11]=1)(=[O:23])[CH3:22]

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 5953292-Acetyl-7-hydroxybenzofuranHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

Product 1

HCID 685406192-acetyl-7-benzofuranyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 37%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

A mixture composed of 1.93 g (14.1 mM) of anhydrous zinc chloride, 1 g (5.7 mM) of 2-acetyl-7-hydroxybenzofuran and 2.2 g of molecular sieve 13× is stirred into 13 ml of toluene and 13 ml of acetonitrile. The mixture is brought to 90° C. and 1.42 g (14.1 mM) of triethylamine and 2.22 g (6.27 mM) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide are added, while maintaining the mixture at the temperature of 90° C. The mixture maintained at 90° C. is then stirred for 20 minutes. The mixture is subsequently cooled, 65 ml of a 0.5 N solution of sodium hydroxide are added, and the resulting mixture is stirred for one hour. The medium is filtered and the precipitate is washed with ethyl acetate. The filtrate is subsequently separated by settling out. The organic phase is washed with a saturated aqueous solution of ammonium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The evaporation residue is purified by silica gel chromatography, elution being carried out with a cyclohexane/ethyl acetate mixture (7/3; v/v). The desired product is obtained in the form of a yellowish solid with a yield of 37%.

Workup

  1. customis brought to 90° C.
  2. temperatureThe mixture maintained at 90° C.
  3. temperatureThe mixture is subsequently cooled
  4. stirringthe resulting mixture is stirred for one hour
  5. filtrationThe medium is filtered
  6. washthe precipitate is washed with ethyl acetate
  7. customThe filtrate is subsequently separated
  8. washThe organic phase is washed with a saturated aqueous solution of ammonium chloride
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe evaporation residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-2e405f8472d949b4ac12d361df7413ef
Source dataset
uspto-grants-2010_01
Patent number
US07652032B2

Linked notes

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