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

HRID 6029
Notes
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Reaction equation

HRID 6029 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][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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 3007857Zinc OxideCatalystHCID 1140TolueneSolvent
HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e7b03201d99f4d3da974587d2d9e325c
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05246961

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes