Propargyl bromide → 4-Trimethylsilylethynyl-1-octyn-4-ol

HRID 848914노트

반응식

HRID 848914 반응식
[Mg].[CH2:2](Br)[C:3]#[CH:4].[CH3:6][Si:7]([C:10]#[C:11][C:12]([CH2:14][CH2:15][CH2:16][CH3:17])=[O:13])([CH3:9])[CH3:8]>CCOCC>[CH3:9][Si:7]([C:10]#[C:11][C:12]([OH:13])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:4][C:3]#[CH:2])([CH3:8])[CH3:6]

참가 물질

5

반응물 3

HCID 7842Propargyl bromide2회HCID 5462224MagnesiumHCID 110195111-Heptyn-3-one, 1-(trimethylsilyl)-

생성물 1

HCID 127861934-Trimethylsilylethynyl-1-octyn-4-ol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a stirred suspension of 1.29 g. of magnesium and 10 mg. of mercuric chloride in 12 ml. of ether is added 0.4 ml. of propargyl bromide. The reaction is initiated after stirring at room temperature for a few minutes. The stirred mixture is cooled in an ice-water bath and a solution of 9.64 g. of n-butyl trimethylsilylethynyl ketone and 3.51 ml. of propargyl bromide in 13 ml. of ether is added, dropwise so that the mixture is very gently boiling during 40 minutes. After addition, the cooling bath is removed and the mixture is stirred at room temperature for 1.5 hours. The mixture is recooled in an ice-bath and 10 ml. of saturated ammonium chloride solution is added. The resulting white mixture is filtered through diatomaceous earth. The clear mother liquid is washed with saturated sodium chloride solution and dried over anhydrous magnesium suflate. The solvent is evaporated to dryness giving 10.5 g. of a red liquid. This liquid is Kugelrohr-distilled at 60° C./0.25-0.3 mm. The pale yellow liquid distillage which is the desired product weights 8.5 g.

후처리

  1. additionTo a stirred suspension of 1.29 g
  2. temperatureThe stirred mixture is cooled in an ice-water bath
  3. additionAfter addition
  4. customthe cooling bath is removed
  5. stirringthe mixture is stirred at room temperature for 1.5 hours
  6. customThe mixture is recooled in an ice-bath
  7. additionof saturated ammonium chloride solution is added
  8. filtrationThe resulting white mixture is filtered through diatomaceous earth
  9. washThe clear mother liquid is washed with saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium suflate
  11. customThe solvent is evaporated to dryness
  12. customgiving 10.5 g
  13. distillationThis liquid is Kugelrohr-distilled at 60° C./0.25-0.3 mm

출처 및 근거

ORD 기록
ord-d859a2630c294f5dbe4b46cb6b1c9988
출처 데이터셋
uspto-grants-1981_10
특허 번호
US04297516

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