Water → Ethyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylate

HRID 1264039

반응식

HRID 1264039 반응식
[CH3:1][O:2][CH:3]=[CH:4][C:5]([O:7][Si](C)(C)C)=[CH2:6].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])C=O.O.FC(F)(F)C(O)=O>C1COCC1.C1(C)C=CC=CC=1>[CH2:17]([O:16][C:12]([CH:1]1[CH2:6][C:5](=[O:7])[CH:4]=[CH:3][O:2]1)=[O:15])[CH3:18]

참가 물질

7

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 70211Ethyl oxoacetateHCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadiene

생성물 1

HCID 22495097Ethyl 4-oxo-3,4-dihydro-2H-pyran-2-carboxylate수율 102.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

ZnCl (0.63 g, 4.6 mmol) was dissolved in anhydrous THF (15 mL) and added to a solution of 1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (7.94 g, 46.0 mmol) and ethyl glyoxalate (7.05 g, 69.0 mmol) in toluene (30 mL) at room temperature. After stirring for 30 minutes, water (30 mL) and TFA (trifluoracetic acid) (2 mL) were added and the mixture was stirred vigorously for 20 min. After concentration, the residue was partitioned between EtOAc (200 mL) and water (100 mL). The separated organic layer was washed with brine, dried over sodium sulfate, and concentrated to give 8.0 g (100%) of brown oil which was carried to the next step without further purification. 1H NMR (CDCl3) δ 1.30 (t, 3H), 2.85 (d, 2H), 4.26 (q, 2H), 5.00 (t, 1H), 5.48 (d, 1H), 7.39 (d, 1H).

후처리

  1. stirringthe mixture was stirred vigorously for 20 min
  2. concentrationAfter concentration
  3. customthe residue was partitioned between EtOAc (200 mL) and water (100 mL)
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-023cdeb999264b938fe982d8f379fd8a
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541481B2

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