Diethyl Ether → 2-[6-(Tetrahydro-pyran-2-yloxy)-hexyl]-malonic acid diethyl ester

HRID 500063

반응식

HRID 500063 반응식
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.CCOCC>C(O)C>[CH2:11]([O:10][C:2](=[O:9])[CH:3]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 7761Diethyl MalonateHCID 3298032-(6-Chlorohexyloxy)tetrahydro-2H-pyranHCID 5360545Sodium

생성물 1

HCID 99976152-[6-(Tetrahydro-pyran-2-yloxy)-hexyl]-malonic acid diethyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

Sodium (1.13 g, 49 mmol) in small quantities was dissolved in dry ethanol (100 ml) with constant stirring under a blanket of dry nitrogen. Diethyl malonate (8.0 g, 50 mmol) was added in one portion and the solution heated at 60° C. for 1 hour. 2-(6-Chloro-hexyloxy)-tetrahydropyran (9.3 g, 42.2 mmol) was added in one portion and the temperature raised to 75-80° C. and maintained at this level for 24 hours. After cooling, the inorganic solid was removed by filtration and solvent evaporated from the filtrate. The residue was dissolved in CH2Cl2 (50 ml), extracted with water (30 ml×2), dried (MgSO4) filtered and volatiles removed to leave a pale yellow oil. This oil was subject to chromatography on silica gel using pet ether 40:60/ether (200:40) as the eluent. The required product eluted with an rf=0.15 and was isolated as a colourless oil. Yield 8.7 g, (60%).

후처리

  1. temperaturethe temperature raised to 75-80° C.
  2. temperaturemaintained at this level for 24 hours
  3. temperatureAfter cooling
  4. customthe inorganic solid was removed by filtration and solvent
  5. customevaporated from the filtrate
  6. dissolutionThe residue was dissolved in CH2Cl2 (50 ml)
  7. extractionextracted with water (30 ml×2)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customvolatiles removed
  11. customto leave a pale yellow oil
  12. washThe required product eluted with an rf=0.15
  13. customwas isolated as a colourless oil

출처 및 근거

ORD 기록
ord-ff87f7792e504deeb53719a718bd290c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767796B2

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