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

HRID 2395867Notes

Reaction equation

HRID 2395867 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, 2H), 3.84 (d, J=4.9 Hz, 2H), 4.44 (s, 4H); 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-30c9d85839fb4bb18795e1d280c3439d
Source dataset
uspto-grants-1996_02
Patent number
US05489700

Reaction notes

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