Water → (S)-2-Azido-1-phenylethanol

HRID 1354390Notes

Reaction equation

HRID 1354390 reaction equation
Cl[CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[N-:11]=[N+:12]=[N-:13].[Na+].O>CS(C)=O.[N-]=[N+]=[N-].[Na+]>[N:11]([CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4])=[N+:12]=[N-:13]

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 6433232-Chloro-1-phenylethanol, (+)-

Product 1

HCID 147803(S)-2-Azido-1-phenylethanolYield 96.8%

Reagents, catalysts & solvents 2

HCID 33557Sodium AzideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

(S)-α-(Chloromethyl)benzenemethanol (2.38 g) in dry DMSO (50 ml) was treated with sodium azide (1.48 g) with stirring then heated at 60° C. for 24 h. More sodium azide (74 mg) was added and heating continued at 80° C. for a further 24 h. The reaction mixture was cooled, poured into water and extracted into ethyl acetate, which was washed with water (3×) then brine and dried (MgSO4). The solvent was evaporated to give the sub-title compound (2.40 g) as a yellow oil.

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted into ethyl acetate, which
  4. washwas washed with water (3×)
  5. dry with materialbrine and dried (MgSO4)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5822db27d1544cb19d219d08f7292d96
Source dataset
uspto-grants-2007_05
Patent number
US07223794B2

Reaction notes

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