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

HRID 593871

반응식

HRID 593871 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 67466404Ethyl 5-cyano-6-methoxy-4-methylpicolinate수율 52.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 SF25-40g, 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]+.

후처리

  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 SF25-40g, 50 to 100% CH2Cl2 in hexanes)

출처 및 근거

ORD 기록
ord-d79a75b0b6074c7495551cd952079718
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242962B2

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