Sodium hydride → 2-Acetyl-2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl ester

HRID 67185노트

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HRID 67185 반응식
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:14](=[O:16])[CH3:15])[CH2:6][CH2:7][C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH3:2].[H-].[Na+].Cl([F:24])(=O)(=O)=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:14](=[O:16])[CH3:15])([F:24])[CH2:6][CH2:7][C:8]#[C:9][Si:10]([CH3:11])([CH3:13])[CH3:12])[CH3:2]

참가 물질

4

반응물 2

HCID 24758Sodium hydrideHCID 130449582-Acetyl-6-(trimethylsilyl)-5-hexynoic acid ethyl ester

생성물 1

HCID 133930802-Acetyl-2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl ester

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

2-acetyl-6-(trimethylsilyl)-5-hexynoic acid ethyl ester (7.1 g) was added to a suspension of sodium hydride (1.0 g) in toluene under a positive argon atmosphere. After stirring for 1 hour, the reaction mixture was cooled to -10° and a mixture of perchloryl fluoride and argon gases was bubbled through the reaction mixture at such a rate that the internal temperature never exceeded 0° C. The perchloryl fluoride addition was discontinued when it ceased to be exothermic. Argon was bubbled through the mixture as it was allowed to warm to room temperature. The reaction mixture was partitioned between hexane and water and the organic phase was dried (MgSO4) and condensed by rotary evaporation to give an oil. The components of the oil were separated by silica gel chromatography using 30% ethyl acetate/hexane as the eluant to give 5.9 g of 2-acetyl-2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl ester. There was also obtained 0.25 g of 2-fluoro-6-(trimethylsilyl)-5-hexynoic acid ethyl ester.

후처리

  1. temperaturethe reaction mixture was cooled to -10°
  2. customwas bubbled through the reaction mixture at such a rate that the internal temperature never exceeded 0° C
  3. additionThe perchloryl fluoride addition
  4. customArgon was bubbled through the mixture as it
  5. customThe reaction mixture was partitioned between hexane and water
  6. customthe organic phase was dried
  7. custom(MgSO4) and condensed
  8. customby rotary evaporation
  9. customto give an oil
  10. customThe components of the oil were separated by silica gel chromatography

출처 및 근거

ORD 기록
ord-e6427a8cf1cb4a8b989b5e628473b81b
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04345084

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