Ethylene carbonate → HCID 54070148, 화합물

HRID 1462963노트

반응식

HRID 1462963 반응식
[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

참가 물질

7

반응물 3

HCID 7303Ethylene carbonateHCID 14798Sodium HydroxideHCID 20452436HCID 20452436, 화합물

생성물 1

HCID 54070148HCID 54070148, 화합물수율 44.4%

시약·촉매·용매 3

HCID 6381Tetramethylammonium iodide촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc877b95a8d846108d00e26e8105f184
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04461907

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