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

HRID 2112135ノート

反応式

HRID 2112135 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21584184Diethylether water溶媒

実験手順

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. 1HNMR (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).

後処理

  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

出典と根拠

ORDレコード
ord-09d16418cdfb4b0f8570d64775ff1162
出典データセット
uspto-grants-2009_04
特許番号
US07521447B2

反応ノート

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