Dimethyl Sulfoxide → (1S)-2-azido-1-(3-chlorophenyl)ethan-1-ol

HRID 2361139Notes

Reaction equation

HRID 2361139 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:21])[CH2:9]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:5]=[CH:6][CH:7]=1.[N-:22]=[N+:23]=[N-:24].[Na+].CS(C)=O>O>[N:22]([CH2:9][C@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[OH:21])=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 15442725toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester

Product 1

HCID 59761679(1S)-2-azido-1-(3-chlorophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of toluene-4-sulfonic acid (S)-2-(3-chlorophenyl)-2-hydroxyethyl ester (16.34 g, 0.050 mol), sodium azide (6.50 g, 0.10 mol) and DMSO (50 mL) was stirred for 2 h at 80° C. Water (100 mL) was added, extracted with hexane-ether (1:1) mixture (2×150 mL). Combined extract was dried over Na2SO4, evaporated. The residue was separated on SiO2 (100 g), hexane-EtOAc, 0 to 20%. Colorless oil, 7.0 g, (0.035 mol, 71%).

Workup

  1. extractionextracted with hexane-ether (1:1) mixture (2×150 mL)
  2. extractionCombined extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated
  5. customThe residue was separated on SiO2 (100 g), hexane-EtOAc, 0 to 20%

Sources & evidence

ORD record
ord-89bce66365aa440bb78d70f401e6c750
Source dataset
uspto-grants-2014_04
Patent number
US08686005B2

Reaction notes

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