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

HRID 1774167

반응식

HRID 1774167 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.C(O)(C(F)(F)F)=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

A solution of ZnCl (0.63 g, 4.6 mmol) in anhydrous THF (15 mL) was 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 (2 mL) were added, and the mixture was stirred vigorously for 20 minutes. 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 4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester (8.0 g, 100% yield) as an oil, which was carried to the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.40 (d, J=1.0 Hz, 1H), 5.48 (d, J=6.5 Hz, 1H), 5.02 (t, J=8.0 Hz, 1H), 4.26 (q, J=7.0 Hz, 2H), 2.85 (d, J=8.0 Hz, 2H), 1.32 (t, J=7.5 Hz 3H); LCMS (ESI) m/z: 171 [M+H]+.

후처리

  1. stirringthe mixture was stirred vigorously for 20 minutes
  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-3673393cd909473d9398f7d252d597c1
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09259470B2

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