Propargyl bromide → 7-Chloro-4-hydroxy-4-methyl-1-heptyne

HRID 1277748

반응식

HRID 1277748 반응식
[Mg].BrC(Br)C.[CH2:6](Br)[C:7]#[CH:8].Cl[CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15].[Cl-:17].[NH4+]>CCOCC>[Cl:17][CH2:6][CH2:7][CH2:8][C:14]([OH:16])([CH3:15])[CH2:13][C:12]#[CH:11]

참가 물질

7

반응물 5

HCID 7842Propargyl bromide2회HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 799932-Pentanone, 5-chloro-HCID 5462224Magnesium

생성물 1

HCID 128987397-Chloro-4-hydroxy-4-methyl-1-heptyne

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
-5 °C

실험 절차

To a mixture of 6.69 g. of magnesium in 20 ml. of ether under argon, is added 0.1 g. of mercuric chloride and 0.1 g. of dibromoethane. The mixture is stirred for 10 minutes and 0.5 ml. of propargyl bromide is added. A 50 ml. portion of ether is added, followed by a solution of 30 g. of 5-chloro-2-pentanone and 32.55 g. of propargyl bromide in 45 ml. of ether with stirring, at a rate to maintain vigorous reflux. The mixture is stirred an additional 15 minutes, cooled to -5° C. and an ice cold saturated solution of ammonium chloride is added dropwise. The ether layer is decanted and filtered. The solids are washed with ether which is also filtered. The combined ether filtrates are washed with water, dried over magnesium sulfate and the solvent removed giving the product as an orange oil.

후처리

  1. additionTo a mixture of 6.69 g
  2. temperatureto maintain vigorous reflux
  3. stirringThe mixture is stirred an additional 15 minutes
  4. customThe ether layer is decanted
  5. filtrationfiltered
  6. washThe solids are washed with ether which
  7. filtrationis also filtered
  8. washThe combined ether filtrates are washed with water
  9. dry with materialdried over magnesium sulfate
  10. customthe solvent removed

출처 및 근거

ORD 기록
ord-feb9c3078a82453f828db91e0537fd1e
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04278806

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