Sodium Azide → 3-Azidomethyl-3-phenoxymethyloxetane

HRID 259852Notes

Reaction equation

HRID 259852 reaction equation
Cl[CH2:2][C:3]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][O:5][CH2:4]1.[N-:15]=[N+:16]=[N-:17].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+].O>[N:15]([CH2:2][C:3]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][O:5][CH2:4]1)=[N+:16]=[N-:17]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 224040183-Chloromethyl-3-phenoxymethyloxetane

Product 1

HCID 224040213-Azidomethyl-3-phenoxymethyloxetaneYield 185.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 516892Sodium BicarbonateCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-chloromethyl-3-phenoxymethyloxetane (20.0 g, 44 mmol), sodium azide (7.35 g, 113 mmol), sodium bicarbonate (0.53 g, 6.3 mmol), tetra-n-butylammonium bromide (0.653 g, 2.0 mmol) and water (41 mL) was heated at about 109° C. to about 113° C. for 16 h. The mixture was cooled and separated. The organic layer was washed with brine solution, diluted with methylene chloride and filtered through a pad of alumina. The solvent was evaporated to give 17.9 g (87%) of 3-azidomethyl-3-phenoxymethyloxetane as an oil that was pure by glc and NMR analysis. NMR: 1H NMR: d 3.71 (s, 2H), 4.07 (s, 2H), 4.42 & 4.46 (AB, J=6.2 Hz, 4H), 6.83-7.21(m, 5H); 13C NMR: d 43.36,53.88, 68.84, 76.18, 114.47, 121.31, 129.50, 158.45; glc Rt=8.13 min.

Workup

  1. temperaturewas heated at about 109° C. to about 113° C. for 16 h
  2. temperatureThe mixture was cooled
  3. customseparated
  4. washThe organic layer was washed with brine solution
  5. additiondiluted with methylene chloride
  6. filtrationfiltered through a pad of alumina
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d544b9d541e04504b257fcd0ee823236
Source dataset
uspto-grants-1996_06
Patent number
US05523424

Reaction notes

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