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

HRID 1656932

反応式

HRID 1656932 の反応式
[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

参加物

7

反応物 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 21059Ethyl Maltol

生成物 1

HCID 105855423-Benzyloxy-2-ethyl-4-pyrone収率 65.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3937bd58a92f491693c6a75d5329f494
出典データセット
uspto-grants-1993_10
特許番号
US05256676

関連ノート

読み込み中…