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

HRID 1640501ノート

反応式

HRID 1640501 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bd630c09c2a449bd99582ee0515eae8f
出典データセット
uspto-grants-2012_02
特許番号
US08114867B2

反応ノート

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