Ethyl formate → Methyl 2-formyl-3-(pyridin-3-yl)propanoate

HRID 45232ノート

反応式

HRID 45232 の反応式
[Na].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.[CH:14](OCC)=[O:15]>CCOCC.O>[CH:14]([CH:9]([CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:15]

参加物

6

反応物 3

HCID 8025Ethyl formateHCID 5360545SodiumHCID 10329646Methyl 3-(pyridin-3-yl)propanoate

生成物 1

HCID 86659740Methyl 2-formyl-3-(pyridin-3-yl)propanoate収率 43.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a suspension of 2.1 g (90.8 mmol) of sodium in 55 mL of anhydrous Et2O is added dropwise, at 0° C. under argon, a mixture of 15 g (90.8 mmol) of methyl 3-(pyridin-3-yl)propanoate and 7.3 mL (57.41 mmol) of ethyl formate. The medium is then stirred for 12 hours at room temperature, taken up in 200 mL of water and extracted with 100 mL of Et2O. The aqueous phase is acidified to pH 5 and then extracted with 2×300 mL of EtOAc. The organic phase is then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a DCM/MeOH gradient of 0 to 10% MeOH. 4.8 g of methyl 2-formyl-3-(pyridin-3-yl)propanoate are obtained in the form of a white solid.

後処理

  1. additionis added dropwise, at 0° C. under argon
  2. extractionextracted with 100 mL of Et2O
  3. extractionextracted with 2×300 mL of EtOAc
  4. dry with materialThe organic phase is then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica gel
  9. washeluting with a DCM/MeOH gradient of 0 to 10% MeOH

出典と根拠

ORDレコード
ord-0f1cea3123f047218baadf1b8123047d
出典データセット
uspto-grants-2013_09
特許番号
US08541455B2

反応ノート

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