Acetic Acid → Ethyl 5-cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylate

HRID 1629804ノート

反応式

HRID 1629804 の反応式
[C:1]([CH2:3][C:4]([NH:6][C:7]([CH3:23])([CH2:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:5])#[N:2].O.[OH-].[Li+].CC(O)=O>C1COCC1.O.CCOC(C)=O>[C:1]([C:3]1[C:4](=[O:5])[NH:6][C:7]([CH3:23])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)#[N:2]

参加物

7

反応物 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86685897Ethyl 2-(2-cyanoacetamido)-2-methyl-4-oxo-4-p-tolylbutanoate

生成物 1

HCID 86685898Ethyl 5-cyano-2-methyl-6-oxo-4-p-tolyl-1,2,3,6-tetrahydropyridine-2-carboxylate収率 115.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Intermediate 108A (1.2837 g, 4.06 mmol) was dissolved in a mixture of THF (15 mL) and water (3.00 mL) in a 25 mL 1 neck pear shaped flask that was equipped with a magnetic stirrer. Lithium hydroxide monohydrate (0.204 g, 4.87 mmol) was added and the reaction mixture was stirred at rt for 1 h. The reaction mixture was acidified to pH 4 with AcOH, diluted with EtOAc (50 mL) and the solution was washed with water (20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give the desired product (1.40 g, 115%) as yellow oil. LCMS Anal. Calc'd for C17H18N2O3 298.1, found [M+H] 299.1.

後処理

  1. customwas equipped with a magnetic stirrer
  2. washthe solution was washed with water (20 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-80e00916ceb048edaf66008081cb30b3
出典データセット
uspto-grants-2014_07
特許番号
US08791091B2

反応ノート

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