Ammonium formate → Ethyl 5-methyl-1H-pyrrole-3-carboxylate

HRID 1967413ノート

反応式

HRID 1967413 の反応式
Cl[C:2]1[NH:3][C:4]([CH3:12])=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([O-])=O.[NH4+]>[C].[Pd].C(O)C>[CH3:12][C:4]1[NH:3][CH:2]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 11008659HCID 11008659、化合物

生成物 1

HCID 12586753Ethyl 5-methyl-1H-pyrrole-3-carboxylate

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒

実験手順

10% palladium carbon (anhydrous) (2.5 g) was suspended with ethanol (500 mL) under argon gas atmosphere. Ethyl 2-chloro-5-methyl-1H-pyrrole-3-carboxylate (50 g; see, Tetrahedron Letters, Vol. 35, No. 33, 5989-5992 (1994)) and ammonium formate (51 g) were added to the reaction mixture at room temperature, and it was stirred at room temperature for 8 hours. The reaction mixture was subjected to filtration with Celite (trade name), the filtrate was concentrated under reduced pressure. Water and ethyl acetate were added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed by water and a saturated aqueous solution of sodium chloride, and concentrated under reduced pressure after drying with anhydrous magnesium sulfate, to thereby obtain a title compound (40 g) having the following physical properties.

後処理

  1. filtrationThe reaction mixture was subjected to filtration with Celite (trade name)
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater and ethyl acetate were added to the obtained residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed by water
  6. concentrationa saturated aqueous solution of sodium chloride, and concentrated under reduced pressure
  7. dry with materialafter drying with anhydrous magnesium sulfate

出典と根拠

ORDレコード
ord-b7b1231543f044eb9f1864a3fe4fa98b
出典データセット
uspto-grants-2013_04
特許番号
US08420810B2

反応ノート

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