Ethyl Acetate → Tert-butyl 5-formylpyrazine-2-carboxylate

HRID 1429631

反応式

HRID 1429631 の反応式
I([O-])(=O)(=O)=O.[Na+].CN(C)/C=[CH:10]/[C:11]1[N:12]=[CH:13][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:15][CH:16]=1.C([O-])(O)=[O:26].[Na+].CCOC(C)=O>C1COCC1.O>[CH:10]([C:11]1[N:12]=[CH:13][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:15][CH:16]=1)=[O:26]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 57475684t-butyl 5-((E)-2-dimethylaminovinyl)pyrazine-2-carboxylate

生成物 1

HCID 57475686Tert-butyl 5-formylpyrazine-2-carboxylate

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

Sodium periodate (1.67 g) was added to a solution of t-butyl 5-((E)-2-dimethylamino-vinyl)-pyrazine-2-carboxylate (645 mg) in 50% THF-water (26 mL), and the mixture was stirred at RT for 4 h. A saturated NaHCO3 solution and EtOAc were added to the reaction solution, and the organic layer was separated. The organic layer was washed with a saturated NaCl solution and dried over anhydrous MgSO4. The insoluble matter was separated by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain the title compound (249 mg). 1H-NMR (CDCl3) δ (ppm): 1.68 (s, 9H), 9.25 (d, J=1.2 Hz, 1H), 9.36 (d, J=1.6 Hz, 1H), 10.2 (s, 1H).

後処理

  1. customthe organic layer was separated
  2. washThe organic layer was washed with a saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-40c5b7bbc2194d2cb85c99d8747453eb
出典データセット
uspto-grants-2015_01
特許番号
US08940734B2

関連ノート

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