Sodium Azide → 3-Azidomethyl-3-methyloxetane

HRID 259851

반응식

HRID 259851 반응식
Cl[CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1.[N-:8]=[N+:9]=[N-:10].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N:8]([CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1)=[N+:9]=[N-:10]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 791123-(Chloromethyl)-3-methyloxetane

생성물 1

HCID 111477193-Azidomethyl-3-methyloxetane수율 93%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

실험 절차

A mixture of 3-chloromethyl-3-methyloxetane (10.1 g, 83.5 mmol), tetra-n-butylammonium bromide (0.308 g, 0.96 mmol), sodium azide (6.5 g, 100 mmol) and water (27 mL) was heated at about 96° C. to about 103° C. for 4.5 h, after which time gas chromatographic analysis of the mixture indicated that the reaction had reached completion. The mixture was cooled to ambient temperature, and extracted with methylene chloride (25 mL). The organic extract was passed through a column containing aluminum oxide (10 g), and the column was rinsed with additional methylene chloride. The solvent was evaporated to give 9.84 g (93% yield) of 3-azidomethyl-3methyloxetane (>99.5% purity by glc and NMR analysis). NMR: 1H NMR: δ1.32 (s, 3H), 3.52 (s, 2H), 4.25 & 4.35 (AB, J=6.0 Hz, 4H); 13C NMR: δ21.44, 58.33, 40.03, 79.76; glc Rt= 3.19 min.

후처리

  1. temperaturewas heated at about 96° C. to about 103° C. for 4.5 h
  2. extractionextracted with methylene chloride (25 mL)
  3. extractionThe organic extract
  4. additioncontaining aluminum oxide (10 g)
  5. washthe column was rinsed with additional methylene chloride
  6. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-49ae46dc72e84376a7d655772ddf8277
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523424

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