Benzyl Chloride → 3-Benzyloxy-2-ethyl-4-pyrone

HRID 1656932

반응식

HRID 1656932 반응식
[CH2:1]([C:3]1[O:4][CH:5]=[CH:6][C:7](=[O:10])[C:8]=1[OH:9])[CH3:2].[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO.O.C(OCC)C>[CH2:13]([O:9][C:8]1[C:7](=[O:10])[CH:6]=[CH:5][O:4][C:3]=1[CH2:1][CH3:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 21059Ethyl Maltol

생성물 1

HCID 105855423-Benzyloxy-2-ethyl-4-pyrone수율 65.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a stirred mixture of 2-ethyl-3-hydroxy-4-pyrone (49 g, 0.35 mol) in methanol (600 ml) and sodium hydroxide (16 g, 0.4 mol) dissolved in water (50 ml) was added benzyl chloride (47.2 ml, 0.41 mol) dropwise at room temperature. After heating under reflux for 48 hours the reaction mixture was cooled, filtered and the filtrate rotary evaporated to provide an oil. The oil was extracted with dichloromethane (300 ml), the solution washed with 5% w/v sodium hydroxide solution (3×250 ml) and water (3×250 ml), then dried over anhydrous sodium sulphate, filtered and rotary evaporated to provide an oil which was dissolved in diethyl ether and crystallized by coating with liquid nitrogen. Recrystallization from diethyl ether gave the title compound as colourless crystals (52.5 g, 65%), m.p. 33°-34° C.

후처리

  1. temperatureAfter heating
  2. temperatureunder reflux for 48 hours the reaction mixture
  3. temperaturewas cooled
  4. filtrationfiltered
  5. customthe filtrate rotary evaporated
  6. customto provide an oil
  7. extractionThe oil was extracted with dichloromethane (300 ml)
  8. washthe solution washed with 5% w/v sodium hydroxide solution (3×250 ml) and water (3×250 ml)
  9. dry with materialdried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. customrotary evaporated
  12. customto provide an oil which
  13. customcrystallized by coating with liquid nitrogen
  14. customRecrystallization from diethyl ether

출처 및 근거

ORD 기록
ord-3937bd58a92f491693c6a75d5329f494
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05256676

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