Toluene → 1-(Aminomethyl)-2,3-dihydro-6-methoxy-1H-inden-1-ol

HRID 231483

反応式

HRID 231483 の反応式
C[Si]([C:5]#[N:6])(C)C.[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2=[O:18])=[CH:11][CH:10]=1.C1(C)C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC.[I-].[Zn+2].[I-]>[OH:18][C:15]1([CH2:5][NH2:6])[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH3:7])[CH:17]=2)[CH2:13][CH2:14]1

参加物

7

反応物 4

HCID 1140TolueneHCID 82115Trimethylsilyl cyanideHCID 3340366-Methoxy-1-IndanoneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 536388371-(Aminomethyl)-2,3-dihydro-6-methoxy-1H-inden-1-ol

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

60 g of trimethylsilyl cyanide are added via syringe to a mixture of 75 g of 6-methoxy-1-indanon, 0.8 g of anhydrous zinc iodide and 150 milliliters of anhydrous toluene. The reaction mixture was heated to 60 degrees Centigrade for 6 hours and then stirred for 16 hours without heating. To a cooled suspension of 44 g of lithium aluminium hydride in 1300 milliliters of anhydrous ether was added the solution of the unpurified cyanohydrin in ether at 0°-5° C. After the addition had been completed the reaction mixture was refluxed with stirring for 21/2 hours. After cooling destruction of the excess lithium aluminium hydride was completed by cautious dropwise addition of 45 milliliters of water followed by dropwise addition of 45 milliliters of 14% sodium-hydroxide solution and subsequent addition of 190 milliliters of water. Stirring was continued for 30 minutes. Filtration and extraction with dichloromethane gave a clear organic solution which was dried over anhydrous magnesium sulphate and evaporated, and the residue was crystallized from ether. Yield: 58 grams of product.

後処理

  1. temperatureThe reaction mixture was heated to 60 degrees Centigrade for 6 hours
  2. temperaturewithout heating
  3. additionAfter the addition
  4. temperaturewas refluxed
  5. stirringwith stirring for 21/2 hours
  6. temperatureAfter cooling
  7. customdestruction of the excess lithium aluminium hydride
  8. additionwas completed by cautious dropwise addition of 45 milliliters of water
  9. additionfollowed by dropwise addition of 45 milliliters of 14% sodium-hydroxide solution and subsequent addition of 190 milliliters of water
  10. stirringStirring
  11. waitwas continued for 30 minutes
  12. filtrationFiltration and extraction with dichloromethane
  13. customgave a clear organic solution which
  14. dry with materialwas dried over anhydrous magnesium sulphate
  15. customevaporated
  16. customthe residue was crystallized from ether

出典と根拠

ORDレコード
ord-7aa45e42112247dabc75def6c4e19170
出典データセット
uspto-grants-1989_07
特許番号
US04847254

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