Acetic Acid → Ethyl 3-(4-methyl-1,3-thiazol-2-yl)-3-oxopropanoate

HRID 254171노트

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HRID 254171 반응식
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[C:11]([C:14]1[S:15][CH:16]=[C:17]([CH3:19])[N:18]=1)(=[O:13])[CH3:12].CC(O)=O>CCCC(C)C.C1(C)C=CC=CC=1.O>[CH3:19][C:17]1[N:18]=[C:14]([C:11](=[O:13])[CH2:12][C:3]([O:7][CH2:8][CH3:9])=[O:10])[S:15][CH:16]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 53247972-Acetyl-4-methylthiazole

생성물 1

HCID 66846879Ethyl 3-(4-methyl-1,3-thiazol-2-yl)-3-oxopropanoate수율 74%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매2회HCID 78922-Methylpentane용매

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온도
80 °C

실험 절차

NaH (60% in oil, 1.34 g, 33.5 mmol) was washed with isohexane (2×14 mL), suspended in toluene (25 mL), treated with diethyl carbonate (4.7 mL, 4.6 g, 38.8 mmol), heated to 80° C., treated dropwise over 20 min with a solution of 2-acetyl-4-methylthiazole (2.72 g, 19.2 mmol) in toluene (5 mL) and stirred at 80° C. for 2 h. The mixture was cooled to 0° C., treated dropwise with HOAc (4.65 mL, 4.9 g, 81 mmol) followed by ice (25 g) and water (50 mL) and stirred for 30 min. The aqueous phase was extracted with toluene (50 mL), the combined organic phase was washed with water (50 mL), dried (MgSO4) and concentrated in vacuo to give the crude product (3 g, 74%) as a dark red oil, used in the next step without further purification; NMR δH (400 MHz, CDCl3) 1.26 (3H, t, J 7.2 Hz), 2.92 (3H, s), 4.14 (2H, s), 4.18-4.25 (2H, m) and 7.31 (1H, s).

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringstirred for 30 min
  3. extractionThe aqueous phase was extracted with toluene (50 mL)
  4. washthe combined organic phase was washed with water (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f39492cb4dc843edad1063bf49cffa23
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875600B2

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