Potassium Carbonate → (E)-3-(benzooxazol-4-yloxy)-but-2-enoic acid ethyl ester

HRID 19388

반응식

HRID 19388 반응식
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([OH:10])=[C:4]2[N:3]=[CH:2]1.[CH2:11]([O:13][C:14](=[O:18])[C:15]#[C:16][CH3:17])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:11]([O:13][C:14](=[O:18])/[CH:15]=[C:16](/[O:10][C:9]1[C:4]2[N:3]=[CH:2][O:1][C:5]=2[CH:6]=[CH:7][CH:8]=1)\[CH3:17])[CH3:12]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 137206971,3-Benzoxazol-4-ol

생성물 1

HCID 66895566(E)-3-(benzooxazol-4-yloxy)-but-2-enoic acid ethyl ester수율 100.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

A stirred mixture of benzooxazol-4-ol (0.388 g, 2.87 mmol), ethyl-2-butynoate (1.93 g, 17.2 mmol) a catalytic amount of 4-dimethylaminopyridine and potassium carbonate (0.595 g, 4.30 mmol) in tetrahydrofuran (20 mL) was placed in a sealed tube and heated at 80° C. for 2 h. The reaction mixture was filtered and the filtrate was collected and concentrated in vacuo. The resulting residue was purified by ISCO column chromatography (Silicycle 40 g, 2% to 15% ethyl acetate/hexanes) which afforded (E)-3-(benzooxazol-4-yloxy)-but-2-enoic acid ethyl ester (710 mg, 100%) as a light yellow solid.

후처리

  1. customwas placed in a sealed tube
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was collected
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by ISCO column chromatography (Silicycle 40 g, 2% to 15% ethyl acetate/hexanes) which

출처 및 근거

ORD 기록
ord-a6e7976868214a29b3b7aa30f68365d0
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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