Sodium Azide → 3-Azidomethyl-3-methyloxetane

HRID 259851ノート

反応式

HRID 259851 の反応式
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]

参加物

5

反応物 2

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

生成物 1

HCID 111477193-Azidomethyl-3-methyloxetane収率 93%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-49ae46dc72e84376a7d655772ddf8277
出典データセット
uspto-grants-1996_06
特許番号
US05523424

反応ノート

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