Oxazole → 3-(Methoxycarbonyl)-5-(1,3-oxazol-2-yl)benzoic Acid

HRID 14118

반응식

HRID 14118 반응식
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.I[C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:20]=1)[C:15]([OH:17])=[O:16]>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[CH3:24][O:23][C:21]([C:19]1[CH:18]=[C:14]([CH:13]=[C:12]([C:2]2[O:1][CH:5]=[CH:4][N:3]=2)[CH:20]=1)[C:15]([OH:17])=[O:16])=[O:22]

참가 물질

6

반응물 3

HCID 9255OxazoleHCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acidHCID 178418339Butyllithium

생성물 1

HCID 210858363-(Methoxycarbonyl)-5-(1,3-oxazol-2-yl)benzoic Acid

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a −70° C. stirred solution of oxazole (432 mg, 6.3 mmol) in tetrahydrofuran (10 mL) is added n-butyllithium (2.5 M in hexanes, 2.75 mL, 6.9 mmol). After 30 min, zinc chloride (1 M in diethyl ether, 18.75 mL, 18.75 mmol) is added and the reaction mixture is warmed to 0° C. for 1 h. To this mixture is added a solution of 3-iodo-5-(methoxycarbonyl)benzoic acid prepared by the method in Example SP-281, step 1 (1.8 g, 6 mmol) in anhydrous tetrahydrofuran (10 mL) followed by palladium(0)tetrakis(triphenylphosphine) (291 mg, 0.25 mmol). The reaction mixture is heated at reflux for 15 h. The reaction mixture is cooled, filtered through diatomaceous earth, diluted with ethyl acetate (50 mL), washed with water, and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 5% methanol/methylene chloride) provides the title compound in pure form. ESI MS m/z 246.1 [M−H]−.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 15 h
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered through diatomaceous earth
  5. additiondiluted with ethyl acetate (50 mL)
  6. washwashed with water, and brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash column chromatography (silica gel, 5% methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-5300a9569b4c4d14bd3a9b5cc261602e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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