Sodium Azide → Methyl 4-azido-3-hydroxybutyrate

HRID 362666

반응식

HRID 362666 반응식
Cl[CH2:2][CH:3]([OH:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[N-:10]=[N+:11]=[N-:12].[Na+]>CN(C)C1C=CN=CC=1.C(C(C)=O)C(C)C>[N:10]([CH2:2][CH:3]([OH:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[N+:11]=[N-:12]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 3629997Methyl 4-chloro-3-hydroxybutanoate

생성물 1

HCID 23630755Methyl 4-azido-3-hydroxybutyrate수율 104.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 7909Methyl Isobutyl Ketone용매

실험 절차

To a mixture of methyl 4-chloro-3-hydroxybutyrate (5 g, 33 mmol), and methyl isobutyl ketone (40 ml) are added sodium azide (2.3 g, 36 mmol) and 4-dimethylaminopyridine (403 mg, 3.3 mmol) and the mixture was refluxed under stirring for 11 hours. After cooling the salt was filtered off and the solvent was distilled off under vacuo and there was obtained methyl 4-azido-3-hydroxybutyrate (5.5 g) as a crude product. And followed by the same procedure as in example 1, there was obtained 4-hydroxy-2-pyrrolidone (2.3 g, 23 mmol, yield:70%). When the above reaction was carried out in the absence of 4-dimethylaminopyridine, it took more than 120 hours to detect the disappearance of the starting materials on gas chromatography.

후처리

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling the salt
  3. filtrationwas filtered off
  4. distillationthe solvent was distilled off under vacuo

출처 및 근거

ORD 기록
ord-e4bf2c4cf45f45a4a1954e8655437745
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05869694

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