Ethyl Acetate → (e)-3-(6-Methoxy-[1,5]naphthyridin-4-yl)-acrylic acid ethyl ester

HRID 1640501노트

반응식

HRID 1640501 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[N:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[CH:15]=O.[CH3:17][C:18](=[O:22])[O:19][CH2:20][CH3:21]>C1COCC1.O>[CH2:20]([O:19][C:18](=[O:22])/[CH:17]=[CH:15]/[C:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH3:3])[N:6]=2)[N:11]=[CH:10][CH:9]=1)[CH3:21]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 665231381,5-Naphthyridine-4-carboxaldehyde, 6-methoxy-

생성물 1

HCID 66736305(e)-3-(6-Methoxy-[1,5]naphthyridin-4-yl)-acrylic acid ethyl ester수율 56%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Triethylphosphonoacetate (7.3 g, 32.6 mmol) was added to a suspension of a NaH dispersion (1.4 g, 32.5 mmol, 55% in paraffin) in THF (40 mL) at 0° C. The mixture was stirred at 0° C. for 20 min before the dropwise addition of 6-methoxy-[1,5]naphthyridine-4-carbaldehyde (4.0 g, 21.3 mmol; prepared as in WO 2006/032466) in THF. The mixture was stirred at rt for 5 h, diluted with water and EA. The phases were separated and the aq. phase extracted with EA (2 times 50 mL). The combined org. phases were washed with brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (Hex/EA 1:1) to give the desired alkene as a colourless solid (3.0 g, 56% yield).

후처리

  1. customThe phases were separated
  2. extractionthe aq. phase extracted with EA (2 times 50 mL)
  3. washphases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on SiO2 (Hex/EA 1:1)

출처 및 근거

ORD 기록
ord-bd630c09c2a449bd99582ee0515eae8f
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114867B2

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