Acetyl chloride → (S)-2-Acetoxy-2-methyl-3,3,3-trifluoropropanoyl chloride

HRID 1062407노트

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HRID 1062407 반응식
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][C@@:6]([CH3:14])([C:10]([F:13])([F:12])[F:11])[C:7](O)=[O:8].C(Cl)(=O)C([Cl:18])=O>C1(C)C=CC=CC=1.C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C@@:6]([CH3:14])([C:10]([F:13])([F:12])[F:11])[C:7]([Cl:18])=[O:8])(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 6367Acetyl chlorideHCID 65578Oxalyl chlorideHCID 2760712(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid

생성물 1

HCID 57462242(S)-2-Acetoxy-2-methyl-3,3,3-trifluoropropanoyl chloride

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

Acetyl chloride (11.7 ml) was added dropwise to a stirred solution of (R)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (10 g) (Method 9) in toluene (100 ml) cooled in an ice bath. The mixture was then heated to 80° C. and the suspension dissolved to give a clear solution. After 2 hours the reaction mixture was cooled and then concentrated to give an oil. This oil was then redissolved in DCM (140 ml) and DMF (4 drops) was added followed by oxalyl chloride (6 ml). The solution bubbled vigorously and the reaction mixture was left to stir for 15 hours. The resultant solution of the title compound was used directly without further purification.

후처리

  1. temperaturecooled in an ice bath
  2. dissolutionthe suspension dissolved
  3. customto give a clear solution
  4. temperatureAfter 2 hours the reaction mixture was cooled
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe solution bubbled vigorously
  8. waitthe reaction mixture was left
  9. customThe resultant solution of the title compound was used directly without further purification

출처 및 근거

ORD 기록
ord-e79f952d56d74546933712c4a9583f6f
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960688B2

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