1,2-Dibromoethane → 4-Hydroxy-4-methyl-oct-1-yn-7-ene

HRID 126727노트

반응식

HRID 126727 반응식
[Mg].Br[CH2:3][CH2:4]Br.[CH2:6](Br)C#C.[O:10]=[C:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15].[Cl-].[NH4+]>CCOCC>[OH:10][C:11]([CH3:6])([CH2:12][CH2:13][CH:14]=[CH2:15])[CH2:16][C:3]#[CH:4]

참가 물질

7

반응물 5

HCID 78391,2-DibromoethaneHCID 7842Propargyl bromide2회HCID 79895-Hexene-2-oneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

생성물 1

HCID 205650044-Hydroxy-4-methyl-oct-1-yn-7-ene

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

A mixture of 19.45 g. of magnesium, 0.15 g. of mercuric chloride and 0.5 ml. of 1,2-dibromoethane in 40 ml. of ether, under argon, is stirred for 5 minutes. A 0.5 ml. portion of propargylbromide is added followed by 160 ml. of ether. To the stirred mixture is added dropwise a solution of 60.0 g. of 5-oxo-1-hexene and 87.3 g. of propargyl bromide in 100 ml. of ether, at such a rate as to maintain a vigorous reflux. After addition is complete, the mixture is stirred for 20 minutes, cooled in an ice-bath and a saturated solution of ammonium chloride is added dropwise. The solid is removed by filtration through Celite and washing with ether. The solvent is removed from the filtrate giving the product as an orange liquid.

후처리

  1. additionA mixture of 19.45 g
  2. additionTo the stirred mixture is added dropwise a solution of 60.0 g
  3. additionAfter addition
  4. temperaturecooled in an ice-bath
  5. customThe solid is removed by filtration through Celite
  6. washwashing with ether
  7. customThe solvent is removed from the filtrate

출처 및 근거

ORD 기록
ord-de79c9b864c7407ba4069d6dced46f0a
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254036

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