Pyridine → 2-(4-(Naphthalen-2-yl)phenyl)acetic acid

HRID 1071286Notes

Reaction equation

HRID 1071286 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.N1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O:23][C:24](=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1>C(OCC)C>[CH:17]1[C:21]2[C:21](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:20]=[CH:19][C:18]=1[C:29]1[CH:30]=[CH:31][C:26]([CH2:25][C:24]([OH:23])=[O:33])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 113690362-(4-(Naphthalen-2-yl)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

Trifluoromethane sulfonic anhydride (32.2 mmol) was added dropwise over 5 minutes to a −40° C. pyridine (70 mL) solution of (4-hydroxy-phenyl)-acetic acid methyl ester (5.35 g, 32.2 mmol). The reaction was stirred at −40° C. for 10 minutes and then at 0° C. for 2 hours. The reaction was diluted with diethyl ether and washed with water and 2N hydrochloric acid. The organic portion was dried over magnesium sulfate and concentrated in vacuo. The crude residue was chromatographed on a Biotage Flash 40M column eluting with ethyl acetate/hexanes (1:4) to provide the title compound as a clear, colorless oil, which crystallized upon standing 9.27 g, 97%). 1H NMR (400 MHz, CDCl3) δ 7.37-7.34 (m, 2H), 7.24-7.21 (m, 2H), 3.70 (3H), 3.64 (2H).

Workup

  1. waitat 0° C. for 2 hours
  2. washwashed with water and 2N hydrochloric acid
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was chromatographed on a Biotage Flash 40M column
  6. washeluting with ethyl acetate/hexanes (1:4)

Sources & evidence

ORD record
ord-a1ddbe63c2f149729e0000b8a5840fe1
Source dataset
uspto-grants-2005_06
Patent number
US06903128B2

Reaction notes

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