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

HRID 909145Notes

Reaction equation

HRID 909145 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9c535e88f1842be8a4845c4e82941a0
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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