Reaction #1929021

ord-ce152e9ac4834ef2a1950f5e2f9b0dd4

Reaction equation

CC(=O)[C@]1(O)[C@](O)(C(C)=O)[C@](CO)(C(C)=O)O[C@](O)(Oc2ccc(C(O)c3ccccn3)cc2)[C@@]1(O)C(C)=O
Tetraacetyl-(p-(pyridinylhydroxymethyl)phenoxy)-β-galactose
O=S(Cl)Cl
SOCl2
→
CC(=O)[C@]1(O)[C@](O)(C(C)=O)[C@](CO)(C(C)=O)O[C@](O)(Oc2ccc(C(Cl)c3ccccn3)cc2)[C@@]1(O)C(C)=O
tetraacetyl-(p-(pyridinylchloromethyl)-phenoxy)-β-galactose

Reactants

CC(=O)[C@]1(O)[C@](O)(C(C)=O)[C@](CO)(C(C)=O)O[C@](O)(Oc2ccc(C(O)c3ccccn3)cc2)[C@@]1(O)C(C)=O
Tetraacetyl-(p-(pyridinylhydroxymethyl)phenoxy)-β-galactose
O=S(Cl)Cl
SOCl2

Reagents

None

Solvents

ClCCl
CH2Cl2

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.WAITthe solution is left
  2. 2
    OtherThe solvent is evaporated under vacuum
  3. 3
    OtherThe product is obtained pure

Procedure

Tetraacetyl-(p-(pyridinylhydroxymethyl)phenoxy)-β-galactose (600 mg, 1.1 mmol) is dissolved in 15 ml of CH2Cl2. SOCl2 (143 mg, 88 μl, 1.2 mmol) is added dropwise and the solution is left stirring for 1 hour. The solvent is evaporated under vacuum. The product is obtained pure and quantitatively.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08945514B2uspto-grants-2015_02