Pyridine → Acetic acid 2-allyl-4-fluorophenyl ester

HRID 1897425노트

반응식

HRID 1897425 반응식
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:2]=[CH2:3].[C:12](OC(=O)C)(=[O:14])[CH3:13].N1C=CC=CC=1>O.CCOCC>[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[O:11][C:12](=[O:14])[CH3:13])[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 113441122-Allyl-4-fluorophenol

생성물 1

HCID 21443045Acetic acid 2-allyl-4-fluorophenyl ester

시약·촉매·용매 1

HCID 21584184Diethylether water용매

실험 절차

To crude (4p), acetic anhydride (36.5 mL, 386.4 mmol) and pyridine (37.5 mL, 463.7 mmol) were added. The resulting mixture was stirred at room temperature for 18 hours, checked by HPLC the next day (reaction appeared mostly complete). The mixture was then poured onto cold H2O/Et2O, the aqueous layer was extracted with Et2O (2×), the combined organic layers were washed sequentially with 10% HCl (3×), saturated NaHCO3 (2×), H2O (2×) and brine, and then dried over anhydrous Na2SO4. After concentration, crude product purity was checked by thin-layer chromatography (hexane/ethyl acetate, 7:3) and HPLC. No mass ion was observed. The crude product (5p) was carried on to next step directly without subsequent purification. 1H NMR (400 MHz, CDCl3) δ 7.04-6.91 (m, 3H), 6.09-5.65 (m, 1H), 5.19-5.06 (m, 2H), 3.27 (d, J=6.26 Hz, 2H), 2.30 (s, CH3).

후처리

  1. customreaction
  2. extractionthe aqueous layer was extracted with Et2O (2×)
  3. washthe combined organic layers were washed sequentially with 10% HCl (3×), saturated NaHCO3 (2×), H2O (2×) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationAfter concentration, crude product purity
  6. customThe crude product (5p) was carried on to next step directly without subsequent purification

출처 및 근거

ORD 기록
ord-a2b316b3d2d54b73bea34c25a9910199
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518983B2

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