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

HRID 238745노트

반응식

HRID 238745 반응식
[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]

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 40715754HCID 40715754, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5730ab9fcb7c45858c934fe18b53941d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642576B2

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