Sodium Hydroxide → Ethyl 5-cyano-6-methoxy-4-methylpicolinate

HRID 42492

反応式

HRID 42492 の反応式
[C:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][C:4]=1[CH3:15])#[N:2].F[B-](F)(F)F.[CH3:21][O+](C)C.[OH-].[Na+]>C(Cl)Cl>[C:1]([C:3]1[C:4]([CH3:15])=[CH:5][C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:7][C:8]=1[O:9][CH3:21])#[N:2]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 275523Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

生成物 1

HCID 67466404Ethyl 5-cyano-6-methoxy-4-methylpicolinate収率 52.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (2.0 g, 9.70 mmol) in CH2Cl2 (25 mL) was added trimethyloxonium tetrafluoroborate (2.0 g, 13.52 mmol). The reaction was rinsed down with CH2Cl2 and stirred at RT for 24 hr. (The reaction eventually cleared up.) To the reaction was added 1N NaOH (75 mL). After stirring for 10 minutes the mixture was poured into a separatory funnel. The CH2Cl2 phase was removed, dried (Na2SO4), filtered and concentrated under vacuum. Purification by silica gel chromatography (Analogix SF25-40 g, 50 to 100% CH2Cl2 in hexanes) gave the product ethyl 5-cyano-6-methoxy-4-methylpicolinate (1.13 g, 5.13 mmol, 52.9% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.75 (s, 1H), 4.37 (q, J=7.1 Hz, 2H), 4.03 (s, 3H), 2.55 (s, 3H), 1.33 (t, J=7.2 Hz, 3H). MS (ES)+m/e 221.2 [M+H]+.

後処理

  1. washThe reaction was rinsed down with CH2Cl2
  2. custom(The reaction
  3. stirringAfter stirring for 10 minutes the mixture
  4. additionwas poured into a separatory funnel
  5. customThe CH2Cl2 phase was removed
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customPurification by silica gel chromatography (Analogix SF25-40 g, 50 to 100% CH2Cl2 in hexanes)

出典と根拠

ORDレコード
ord-4b05ac5603cb4e539fbbd7027a79c093
出典データセット
uspto-grants-2013_09
特許番号
US08536179B2

関連ノート

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