Potassium Carbonate → 2-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester

HRID 1269491노트

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HRID 1269491 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 688835012-Methyl-2-(3-pyridin-3-yl-phenoxy)-propionic acid ethyl ester수율 78.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

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온도
95 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-35d1c191d8dc4ec6925e2b50f0d27a9b
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199243B2

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