Potassium Carbonate → 4-Ethyl-3-(3-trifluoromethoxy-propoxy)-benzoic acid methyl ester

HRID 1158476Notes

Reaction equation

HRID 1158476 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.[F:14][C:15]([F:29])([F:28])[O:16][CH2:17][CH2:18][CH2:19]OS(C(F)(F)F)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([O:12][CH2:19][CH2:18][CH2:17][O:16][C:15]([F:29])([F:28])[F:14])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 54428408Methyl 4-ethyl-3-hydroxybenzoateHCID 754063563-(Trifluoromethoxy)propyl trifluoromethanesulfonate

Product 1

HCID 686167234-Ethyl-3-(3-trifluoromethoxy-propoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-ethyl-3-hydroxy-benzoic acid methyl ester (250 mg, 1.32 mmol), crude trifluoro-methanesulfonic acid 3-trifluoromethoxy-propyl ester (590 mg, 1.58 mmol; purity of 74%) and anhydrous K2CO3 (276 mg, 1.98 mmol) in MeCN (2.0 mL) is stirred in a sealed glass vial overnight at room temperature. The crude product obtained after filtration and evaporation is purified by flash chromatography (hexane/AcOEt 1:1) to give the title compound as oil. TLC, Rf (hexane/AcOEt 3:1)=0.38. 1H-NMR (CDCl3): δ 1.24 (t, 3H), 2.25 (m, 2H), 2.70 (q, 2H), 3.94 (s, 3H), 4.18 (t, 2H), 4.24 (t, 2H), 7.25 (d, 1H), 7.52 (s, 1H), 7.64 (d, 1H) ppm. 19F-NMR (CDCl3): δ −61.1 ppm.

Workup

  1. customThe crude product obtained
  2. filtrationafter filtration and evaporation
  3. customis purified by flash chromatography (hexane/AcOEt 1:1)

Sources & evidence

ORD record
ord-f9458b3f02364450a14e38676df1b515
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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