HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Hydroxybenzonitrile → 2-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Hydroxybenzonitrile | HCID 11907 | — |
| Reactant | 2,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide | HCID 10926314 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Catalyst | Silver imidazolate | HCID 10931941 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside | HCID 15067854 | 20% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05246961 |
| Source dataset | uspto-grants-1993_09 |
| ORD ID | ord-231454abe7284d98adfcccdd34ddb1a5 |
| Source note | uspto-grants-1993_09 |