Potassium Iodide → 4-(3-Cyanopropoxy)-7H-furo[3,2-g][1]benzopyran-7-on

HRID 225977

反応式

HRID 225977 の反応式
[CH:1]1[C:5]2=[C:6]([OH:15])[C:7]3[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=3[CH:9]=[C:4]2[O:3][CH:2]=1.Cl[CH2:17][CH2:18][CH2:19][C:20]#[N:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[C:20]([CH2:19][CH2:18][CH2:17][O:15][C:6]1[C:7]2[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=2[CH:9]=[C:4]2[O:3][CH:2]=[CH:1][C:5]=12)#[N:21]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123364-ChlorobutyronitrileHCID 5280371Bergaptol

生成物 1

HCID 117017304-(3-Cyanopropoxy)-7H-furo[3,2-g][1]benzopyran-7-on

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

800 mg (3.956 mmol) of 5-hydroxypsoralen and 0.7 ml (655.5 mg, 6.33 mmol) of 4-chlorobutyronitrile were refluxed in 50 ml of 2-butanone in the presence of an excess (2.6 g) of anhydrous potassium carbonate and catalytic amounts of potassium iodide for 48 hours. The progress of the reaction was monitored by thin layer chromatography. After 48 hours the reaction mixture was concentrated under reduced pressure. The residual oily layer was cooled, diluted with water and acidified with concentrated hydrochloric acid to pH 1. The slurry was stirred for 15-20 min and then filtered. The solids were washed with water to neutral pH, dried bysuction and then further washed with petroleum ether. The dried solids were dissolved in refluxing methanol, treated with charcoal and recrystallized from methanol.

後処理

  1. concentrationAfter 48 hours the reaction mixture was concentrated under reduced pressure
  2. temperatureThe residual oily layer was cooled
  3. additiondiluted with water
  4. filtrationfiltered
  5. washThe solids were washed with water to neutral pH
  6. customdried bysuction
  7. washfurther washed with petroleum ether
  8. dissolutionThe dried solids were dissolved
  9. temperaturein refluxing methanol
  10. additiontreated with charcoal
  11. customrecrystallized from methanol

出典と根拠

ORDレコード
ord-1dbfc873fb324ad7975bc266acc8a3b3
出典データセット
uspto-grants-2009_07
特許番号
US07557138B2

関連ノート

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