Thionyl Chloride → 5-p-Methoxybenzyloxy-2-chloromethyl-4-pyrone

HRID 1461238ノート

反応式

HRID 1461238 の反応式
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:17])[CH:11]=[C:12]([CH2:15]O)[O:13][CH:14]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:22])=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][Cl:22])[O:13][CH:14]=2)=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-

生成物 1

HCID 199802145-p-Methoxybenzyloxy-2-chloromethyl-4-pyrone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

5-p-Methoxybenzyloxy-2-hydroxymethyl-4-pyrone, 24 g, was dissolved in 120 ml of dry tetrahydrofuran. The solution was cooled to 5° C. and 15 ml of thionyl chloride was dropwise added to the solution over 30 minutes. The reaction solution was stirred at the same temperature for 3 hours. After completion of the reaction, the reaction liquid was concentrated to approximately 20 ml and the concentrate was added to 50 ml of water and 100 ml of dichloromethane. Under ice cooling, the pH was adjusted to 7.0 with saturated sodium hydrogencarbonate aqueous solution and the organic phase was washed with 20 ml of water. After drying over anhydrous magnesium sulfate, the organic phase was concentrated under reduced pressure and crystallized with ethyl acetate-ether. The formed crystals were taken out by filtration and dried under reduced pressure to give 20 g of the title compound.

後処理

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. concentrationwas concentrated to approximately 20 ml
  4. additionthe concentrate was added to 50 ml of water and 100 ml of dichloromethane
  5. washthe organic phase was washed with 20 ml of water
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. concentrationthe organic phase was concentrated under reduced pressure
  8. customcrystallized with ethyl acetate-ether
  9. filtrationThe formed crystals were taken out by filtration
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-7b01259a04a3496db4dc228bad4672f6
出典データセット
uspto-grants-1991_12
特許番号
US05075299

反応ノート

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