Ethylene carbonate → HCID 54070148、化合物

HRID 1462963ノート

反応式

HRID 1462963 の反応式
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]2)=[CH:4][CH:3]=1.C1(=O)O[CH2:21][CH2:20][O:19]1.[OH-].[Na+]>[I-].C[N+](C)(C)C.O.C(O)C>[OH:19][CH2:20][CH2:21][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7]2)=[CH:16][CH:17]=1

参加物

7

反応物 3

HCID 7303Ethylene carbonateHCID 14798Sodium HydroxideHCID 20452436HCID 20452436、化合物

生成物 1

HCID 54070148HCID 54070148、化合物収率 44.4%

試薬・触媒・溶媒 3

HCID 6381Tetramethylammonium iodide触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

4'-Hydroxyflavan (2.26 g.), ethylene carbonate (8.8 g.) and tetramethylammonium iodide (0.30 g.) were heated together at 140° C. for 4 hrs. Sodium hydroxide (6.5 g) in water (20 ml.) and ethanol (250 ml.) was added, and the solution boiled under reflux for 5 hrs. The solution was filtered, diluted with water, and extracted 3 times with ether. The combined extracts were dried and evaporated, and the residue chromatographed on neutral alumina. The product was eluted with chloroform and after evaporation of the solvent was recrystallised from 60°-80° C. petroleum ether to yield 4'-(2-hydroxyethoxy) flavan (1.2 g.) m.p. 84°-85° C.

後処理

  1. temperatureunder reflux for 5 hrs
  2. filtrationThe solution was filtered
  3. additiondiluted with water
  4. extractionextracted 3 times with ether
  5. customThe combined extracts were dried
  6. customevaporated
  7. customthe residue chromatographed on neutral alumina
  8. washThe product was eluted with chloroform
  9. customafter evaporation of the solvent
  10. customwas recrystallised from 60°-80° C. petroleum ether

出典と根拠

ORDレコード
ord-dc877b95a8d846108d00e26e8105f184
出典データセット
uspto-grants-1984_07
特許番号
US04461907

反応ノート

読み込み中…