Potassium Carbonate → 2,5-Dimethylfuran-3-carboxylic Acid 2-Methoxyethoxymethyl Ester

HRID 723731노트

반응식

HRID 723731 반응식
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22]Cl>CN(C=O)C.O>[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22][O:8][C:7]([C:6]1[CH:5]=[C:4]([CH3:10])[O:3][C:2]=1[CH3:1])=[O:9]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 694652,5-Dimethyl-3-furoic acidHCID 775901-(Chloromethoxy)-2-methoxyethane

생성물 1

HCID 587458882,5-Dimethylfuran-3-carboxylic Acid 2-Methoxyethoxymethyl Ester수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A 2 L round-bottomed flask equipped with a mechanical stirrer was charged with 2,5-dimethyl-3-furoic acid (81.0 g, 0.58 mol) and potassium carbonate (95.9 g, 0.69 mol) in DMF (500 mL). An ice bath was used to cool the reaction as 2methoxyethoxymethyl chloride (72.2 g, 0.58 mol) was added portionwise. The reaction was stirred for 5 h at rt. The mixture was then diluted with water (1.5 L) and extracted with EtOAc (2×600 mL). The combined organics were washed with water (2×900 mL) and saturated sodium chloride solution (1 L), dried over MgSO4, filtered and concentrated to afford compound 803A (103 g, 82%) as a yellow oil. 1H NMR(CDCl3): δ=6.23 (s, 1H), 5.47 (s, 1H), 3.84 (m, 2H), 3.56 (m, 2H), 3.38 (s, 3H), 2.51 (s, 3H) and 2.20 ppm (s, 3H).

후처리

  1. customA 2 L round-bottomed flask equipped with a mechanical stirrer
  2. customAn ice bath was used
  3. temperatureto cool
  4. additionwas added portionwise
  5. extractionextracted with EtOAc (2×600 mL)
  6. washThe combined organics were washed with water (2×900 mL) and saturated sodium chloride solution (1 L)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-280e921f30e6419fafea1d67eba91f51
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141578B2

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