Potassium Carbonate → HCID 68883501, compound

HRID 1269491Notes

Reaction equation

HRID 1269491 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH:2]=1.Br[C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH2:19]([O:18][C:16](=[O:17])[C:15]([CH3:22])([O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:8]=1)[CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 129379483-(Pyridin-3-yl)phenol

Product 1

HCID 68883501HCID 68883501, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-pyridin-3-yl-phenol (5.14 g, 30.0 mmol), ethyl 2-bromoisobutyrate (26.3 g, 135.0 mmol), and K2CO3 (18.7 g, 135.0 mmol) in anhydrous DMF (60 mL) was heated at 95° C. under nitrogen for 5 h. After cooling, brine (200 mL) was added and the mixture was extracted with ethyl acetate (250 mL). The separated organic layer was washed with brine, filtered, and concentrated. The oil residue was taken up in 80 mL of 3 M HCl, stirred for 15 min, diluted with brine (100 mL), and extracted with ethyl acetate (2×150 mL). The separated aqueous layer was cooled in ice/water bath, adjusted to pH 10 with solid Na2CO3, and extracted with ethyl acetate (2×200 mL). The organic extract was dried over sodium sulfate and concentrated to afford 6.70 g (78%) of 2-methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester as a light brown oil: 1H NMR (CDCl3) δ 1.22 (t, 3H), 1.61 (s, 6H), 4.22 (q, 2H), 6.82 (dd, 1H), 7.08 (s, 1H), 7.20 (dd, 1H), 7.38 (m, 2H), 7.81 (dd, 1H), 8.59 (br s, 1H), 8.80 (br s, 1H); MS m/z (relative intensity) 285 (M+, 11), 212 (22), 171 (100).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate (250 mL)
  3. washThe separated organic layer was washed with brine
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additiondiluted with brine (100 mL)
  7. extractionextracted with ethyl acetate (2×150 mL)
  8. temperatureThe separated aqueous layer was cooled in ice/water bath
  9. extractionextracted with ethyl acetate (2×200 mL)
  10. extractionThe organic extract
  11. dry with materialwas dried over sodium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-35d1c191d8dc4ec6925e2b50f0d27a9b
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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