Sodium Azide → [3-(Azidomethyl)oxetan-3-yl]methanol

HRID 259853

Reaction equation

HRID 259853 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>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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 2

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

Product 1

HCID 22404019[3-(Azidomethyl)oxetan-3-yl]methanolYield 49%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A solution of sodium azide (2.07 g, 0.0317 mol), 3-bromomethyl-3-hydroxymethyloxetane (5.0 g, 0.028 mol) and tetra-n-butylammonium bromide (0.0978 g, 0.3 mmol) in water (14 mL) was heated for 3 h at 104°-107° C. The solution was cooled and was extracted with ethyl ether (5×20 mL). The combined extracts were evaporated to give 1.92 g (49%) of 3-azidomethyl-3-hydroxymethyloxetane, essentially pure by glc analysis, as an oil. NMR: 1H NMR: 3.70 (s, 2H), 3.84 (d, J=4.9 Hz, 2H), 4.44 (s, 4H); 13C NMR: 44.283, 53.852, 64.073, 76.227.

Workup

  1. temperatureThe solution was cooled
  2. extractionwas extracted with ethyl ether (5×20 mL)
  3. customThe combined extracts were evaporated

Sources & evidence

ORD record
ord-f9bbc3e78efd49998b60d6c278c7286a
Source dataset
uspto-grants-1996_06
Patent number
US05523424

Linked notes

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