Ammonium Chloride → (2S)-1-Azido-4,4,4-trifluoro-2-butanol

HRID 238745ノート

反応式

HRID 238745 の反応式
[F:1][C:2]([F:8])([F:7])[CH2:3][C@H:4]1[CH2:6][O:5]1.[N-:9]=[N+:10]=[N-:11].[Na+].[NH4+].[Cl-]>CCO.O>[N:9]([CH2:6][C@@H:4]([OH:5])[CH2:3][C:2]([F:8])([F:7])[F:1])=[N+:10]=[N-:11]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 40715754HCID 40715754、化合物

生成物 1

HCID 59459514(2S)-1-Azido-4,4,4-trifluoro-2-butanol収率 83.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

To a solution of (S)-2-(2,2,2-trifluoroethyl)oxirane (2.00 g, 16.0 mmol) in a mixture of EtOH (16 mL) and H2O (4 mL) were added NaN3 (2.06 g, 32.0 mmol) and NH4Cl (1.70 g, 32.0 mmol). After stirring at room temperature for 18 h, the reaction mixture was diluted with H2O (50 mL), extracted with Et2O (2×75 mL). The combined organic layer was dried over MgSO4, filtered and concentrated to give (S)-1-azido-4,4,4-trifluorobutan-2-ol as an oil (2.26 g, 83% yield). NMR: 400 MHz 1H (CDCl3) 4.17 ppm, 1H, ddd, J=6.81, 3.74, 3.52 Hz; 3.48 ppm, 1H, m; 3.37 ppm, 1H, m; 2.35 ppm, 2H, m.

後処理

  1. extractionextracted with Et2O (2×75 mL)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-5730ab9fcb7c45858c934fe18b53941d
出典データセット
uspto-grants-2014_02
特許番号
US08642576B2

反応ノート

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