Sodium Acetate → (E)-(2-Styryloxazol-4-yl)methanol

HRID 322299

반응식

HRID 322299 반응식
Cl[CH2:2][C:3]1[N:4]=[C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:6][CH:7]=1.C([O-])(=[O:18])C.[Na+]>CN(C)C=O>[C:10]1(/[CH:9]=[CH:8]/[C:5]2[O:6][CH:7]=[C:3]([CH2:2][OH:18])[N:4]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 517045Sodium AcetateHCID 220097524-Chloromethyl-2-styryl-oxazole

생성물 1

HCID 13657827(E)-(2-Styryloxazol-4-yl)methanol수율 91.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 4-chloromethyl-2-[(E)-2-phenylethenyl]oxazole (5.0 g), sodium acetate (7.48 g) and N,N-dimethylformamide (50 ml) was stirred at 90° C. for 4.5 hours. The reaction mixture was poured onto ice-water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water dried (MgSO4), and concentrated under reduced pressure. To the residue was added potassium carbonate (4.73 g), water (25 ml) and methanol (50 ml) and then the resultant was stirred for 2 hours at room temperature. The reaction mixture was concentrated, to which was added brine, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 2-[(E)-2-phenylethenyl]-4-oxazolylmethanol (4.18 g, 91%). Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 94-95° C.

후처리

  1. additionThe reaction mixture was poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added potassium carbonate (4.73 g), water (25 ml) and methanol (50 ml)
  7. stirringthe resultant was stirred for 2 hours at room temperature
  8. concentrationThe reaction mixture was concentrated, to which
  9. additionwas added brine
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with water
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c5358636fe4f4ed4ace4be461aad04ea
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211215B1

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