Acetyl chloride → Methyl (furan-3-yl)acetate

HRID 372913노트

반응식

HRID 372913 반응식
C(C1[CH:7]=[CH:6][O:5][CH:4]=1)=O.CS(CSC)=O.[OH-:14].C([N+](C)(C)C)[C:16]1[CH:21]=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27]>CO.C1COCC1.O>[O:28]1[CH:16]=[CH:21][C:27]([CH2:7][C:6]([O:5][CH3:4])=[O:14])=[CH:26]1

참가 물질

8

반응물 4

HCID 6367Acetyl chlorideHCID 103513-FuraldehydeHCID 66854Benzyltrimethylammonium hydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfide

생성물 1

HCID 12327271Methyl (furan-3-yl)acetate수율 36%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A mixture of 3-formylfuran (5.0 g), methyl (methylthiomethyl)sulphoxide (7.lg) and Triton B [(40 weight % solution of benzyltrimethylammonium hydroxide in methanol) 4.8 g] in THF (7 ml) was heated under reflux for 5 hours. After cooling, it was poured into water and extracted with ether. The extracts were washed with water (× 3) and then with aqueous sodium chloride, then dried and concentrated to give a brown oil (4.Og), IR (film) 1610, 1060 cm-1 . Acetyl chloride (1.4 ml) was added carefully with stirring to dry methanol (25 ml), cooled to 0° C. Following the addition, the resulting mixture was allowed to warm to room temPerature, and part of the brown oil (2.0g) was added to it in one portion with stirring. After 30 minutes, the resulting mixture was heated at 100° C. under reflux for 2 hours, then allowed to cool, poured into water and extracted with ether. The extracts were washed successively with water (× 3), aqueous sodium bicarbonate and aqueous sodium chloride, then dried, concentrated, and eluted through a short column of silica gel using a 1:1 mixture of ether and petrol to give methyl (3-furyl)acetate (1.3 g, 36% yield from 3-formylfuran) as a yellow oil, IR (film) 1736 cm-1.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with ether
  5. washThe extracts were washed with water (× 3)
  6. dry with materialwith aqueous sodium chloride, then dried
  7. concentrationconcentrated
  8. customto give a brown oil (4.Og), IR (film) 1610, 1060 cm-1
  9. additionthe addition
  10. temperatureto warm to room temPerature
  11. temperaturethe resulting mixture was heated at 100° C.
  12. temperatureunder reflux for 2 hours
  13. temperatureto cool
  14. extractionextracted with ether
  15. washThe extracts were washed successively with water (× 3), aqueous sodium bicarbonate and aqueous sodium chloride
  16. customdried
  17. concentrationconcentrated
  18. washeluted through a short column of silica gel using
  19. additiona 1:1 mixture of ether and petrol

출처 및 근거

ORD 기록
ord-302f6dc301df45d2ad6e145baca28671
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05160364

반응 노트

불러오는 중…