Propargyl bromide → 5-Hydroxy-7-propargyloxy-2,2-dimethyl-4-chromanone

HRID 1073387노트

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HRID 1073387 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]#[CH:9].[OH:11][C:12]1[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]2[C:13]=1[C:14](=[O:25])[CH2:15][C:16]([CH3:24])([CH3:23])[O:17]2>CC(CC)=O.[I-].[K+]>[OH:11][C:12]1[CH:21]=[C:20]([O:22][CH2:9][C:8]#[CH:7])[CH:19]=[C:18]2[C:13]=1[C:14](=[O:25])[CH2:15][C:16]([CH3:23])([CH3:24])[O:17]2

참가 물질

6

반응물 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 8213625,7-Dihydroxy-2,2-dimethylchroman-4-one

생성물 1

HCID 145929635-Hydroxy-7-propargyloxy-2,2-dimethyl-4-chromanone수율 75%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6569Methyl Ethyl Ketone용매

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온도
0 °C

실험 절차

In 60 ml of methyl-ethyl-ketone 4.2 g of 5,7-dihydroxy-2,2-dimethyl-4-chromanone are dissolved, whereupon 3.0 g (22 millimoles) of potassium carbonate, 0.2 g of potassium iodide, and 3.0 g (2.3 ml, 25 millimoles) of propargyl bromide are added and the reaction mixture is reflexed for 4 hours. The inorganic salt is filtered off, the residue is taken up in 100 ml of carbon tetrachloride and extracted twice with 25 ml of a 5% sodium hydroxide solution each. The aqueous-alkaline layer is cooled to 0° C. The aqueous-alkaline layer is cooled to 0° C. The precipitated sodium phenolate salt is filtered off, washed twice with 20 ml of acetone each, and suspended in 25% hydrochloric acid (50 ml). The mixture is stirred at 5° C. for an hour. The precipitated white product is filtered off, washed twice with 20 ml of water each and dried to constant weight. The crude product thus obtained can be directly subjected to further reactions. Thus 3.7 g of the desired compound are obtained, yield 75% Mp.: 122°-124° C.

후처리

  1. additionare added
  2. filtrationThe inorganic salt is filtered off
  3. extractionextracted twice with 25 ml of a 5% sodium hydroxide solution each
  4. temperatureThe aqueous-alkaline layer is cooled to 0° C
  5. filtrationThe precipitated sodium phenolate salt is filtered off
  6. washwashed twice with 20 ml of acetone each, and
  7. filtrationThe precipitated white product is filtered off
  8. washwashed twice with 20 ml of water each and
  9. customdried to constant weight
  10. customThe crude product thus obtained can

출처 및 근거

ORD 기록
ord-56d9670cf8794dc6a526caf07d1572f8
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04968819

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