Oxazole → Methyl 4-(oxazol-2-yl)benzoate

HRID 348886

반응식

HRID 348886 반응식
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.I[C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1>O1CCCC1.C(OCC)C.[Cl-].[Zn+2].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

참가 물질

8

반응물 3

HCID 9255OxazoleHCID 69273Methyl 4-iodobenzoateHCID 178418339Butyllithium

생성물 1

HCID 21985208Methyl 4-(oxazol-2-yl)benzoate

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a −70° C., stirred solution of oxazole (190 μL, 3.8 mmol) in tetrahydrofuran (10 mL) is added n-butyl lithium (2.6 mL of a 1.6 M solution in hexanes, 4.2 mmol). After 30 min, zinc chloride (11.5 mL of a 1.0 M solution in diethyl ether, 11.5 mmol) is added. The reaction mixture is warmed to 0° C. and methyl 4-iodobenzoate (1 g, 3.8 mmol) and palladium(0) tetrakis(triphenylphosphine) (530 mg, 0.4 mmol) are added. The reaction mixture is heated at 70° C. for 20 h under argon, cooled to room temperature, and then partitioned between ethyl acetate and water. The organic layer is washed with water and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (3:1 hexanes/ethyl acetate) yields the title compound. 1H NMR (300 MHz, CDCl3) δ 8.14 (s, 4H), 8.07–8.05 (m, 1H), 7.36–7.35 (m, 1H), 3.95 (s, 3H).

후처리

  1. temperatureThe reaction mixture is heated at 70° C. for 20 h under argon
  2. temperaturecooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (3:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-a365ede3aea64662875489703c4188a0
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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