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

HRID 1073387ノート

反応式

HRID 1073387 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-56d9670cf8794dc6a526caf07d1572f8
出典データセット
uspto-grants-1990_11
特許番号
US04968819

反応ノート

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