Methyl Acrylate → Methyl beta-hydroxy-alpha-methylene-2-pyridinepropanoate

HRID 1021879노트

반응식

HRID 1021879 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11]>N12CCN(CC1)CC2.C(Cl)(Cl)Cl>[OH:8][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10](=[CH2:11])[C:9]([O:13][CH3:14])=[O:12]

참가 물질

5

반응물 2

HCID 7294Methyl AcrylateHCID 142732-Pyridinecarboxaldehyde

생성물 1

HCID 11008779Methyl beta-hydroxy-alpha-methylene-2-pyridinepropanoate수율 60%

시약·촉매·용매 2

HCID 9237Dabco촉매HCID 6212Chloroform용매

실험 절차

A 250-mL single-neck round-bottomed flask was charged with chloroform (100 mL), picolinaldehyde (10.7 g, 0.10 mol), methyl acrylate (8.60 g, 0.10 mol), and 1,4-diaza-bicyclo[2.2.2]octane (0.560 g, 5.00 mmol). The reaction mixture stirred at room temperature for 48 h. After this time the reaction was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 3:1 petroleum ether/ethyl acetate to afford 193a as dark yellow oil (11.6 g, 60%). MS-ESI: (M+H)+ 194.2. 1H NMR (500 MHz, CDCl3) δ 8.54 (d, J=5.0 Hz, 1H), 7.69-7.66 (m, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.22-7.20 (m, 1H), 6.36 (s, 1H), 5.97 (s, 1H), 5.62 (s, 1H), 4.85 (s, 1H), 3.74 (s, 3H).

후처리

  1. concentrationAfter this time the reaction was concentrated under reduced pressure
  2. customthe residue was purified by silica-gel column chromatography
  3. washeluting with 3:1 petroleum ether/ethyl acetate

출처 및 근거

ORD 기록
ord-bbd646cef78e47e7bcddf749c160d065
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716274B2

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