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

HRID 6041

Reaction equation

HRID 6041 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]([O:13][C@@H:14]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@@H:15]1Br)(=[O:12])[CH3:11]>C(Cl)Cl.[N-]1C=CN=C1.[Ag+].[Cl-].[Zn+2].[Cl-]>[C:10]([O:13][C@@H:14]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@H:15]1[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])(=[O:12])[CH3:11]

Participants

6

Reactant 2

HCID 119072-HydroxybenzonitrileHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Product 1

HCID 150678542-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranosideYield 20%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 10931941Silver imidazolateCatalystHCID 6344DichloromethaneSolvent

Procedure

If the procedure described in Preparation LXXXIII is followed starting from 2 g (16.8.10-3 mol) of 2-hydroxybenzonitrile, 4.4 g (25.1.10-3 mol) of silver imidazolate, 6.5 g (18.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4.6 g (33.6.10-3 mol) of zinc chloride in 80 ml of methylene chloride, 1.32 g (yield: 20%) of the expected product are obtained after purification by chromatography on silica gel using a toluene/ethyl acetate mixture (6/1 v/v) as the eluent, and precipitation in ether.

Workup

  1. customIf the procedure described in Preparation LXXXIII

Sources & evidence

ORD record
ord-231454abe7284d98adfcccdd34ddb1a5
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

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