Acetone → [3-(Azidomethyl)oxetan-3-yl]methanol

HRID 2211203Notes

Reaction equation

HRID 2211203 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1([CH2:11][OH:12])[CH2:10][O:9][CH2:8]1.CC(C)=O>O>[N:1]([CH2:6][C:7]1([CH2:11][OH:12])[CH2:10][O:9][CH2:8]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 529264[3-(Bromomethyl)oxetan-3-yl]methanol

Product 1

HCID 22404019[3-(Azidomethyl)oxetan-3-yl]methanolYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of sodium azide (9.5 g, 0.14 mol), 3-bromomethyl-3-hydroxymethyloxetane (24.0 g, 0.14 mol), 20 mL of acetone and 20 mL of water was refluxed for 12 h. The acetone was evaporated and the resulting residue was extracted with two portion of 40 mL of ethyl acetate. The combined organic extracts were dried over magnesium sulfate (MgSO4). The solvent was removed by evaporation. 18.0 g, representing a 94% yield, of 3-azidomethyl-3-hydroxymethyloxetane were obtained as an oil. This oil was found to be essentially pure by gas-liquid chromatography (GLC) analysis. NMR: 1H NMR 3.70 (s, 2 H), 3.84 (d, J=4.9 Hz, 2 H), 4.44 (s, 4 H); 13C NMR 44.283, 53,852, 64,073, 76.227.

Workup

  1. temperaturewas refluxed for 12 h
  2. customThe acetone was evaporated
  3. extractionthe resulting residue was extracted with two portion of 40 mL of ethyl acetate
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate (MgSO4)
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-63352e062898433080a66f5c7766bb63
Source dataset
uspto-grants-1995_10
Patent number
US05463019

Reaction notes

Loading…