Sodium Methoxide → 6-(2,6-Diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester

HRID 1392619ノート

反応式

HRID 1392619 の反応式
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[C:10](Cl)=[CH:9][C:8]([C:12]2[C:17]([CH2:18][CH3:19])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:20][CH3:21])=[N:7][C:6]=1[CH3:22])C.[CH3:24][O-:25].[Na+]>>[CH3:1][O:3][C:4](=[O:23])[C:5]1[C:10]([O:25][CH3:24])=[CH:9][C:8]([C:12]2[C:13]([CH2:20][CH3:21])=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:18][CH3:19])=[N:7][C:6]=1[CH3:22]

参加物

3

反応物 2

HCID 10942334Sodium MethoxideHCID 59678345Ethyl 4-chloro-6-(2,6-diethylphenyl)-2-methylnicotinate

生成物 1

HCID 596783046-(2,6-Diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester

反応条件

温度
65 °C

実験手順

A mixture of 4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-nicotinic acid ethyl ester (165 mg, 0.5 mmol) and sodium methoxide (0.5 M in methanol, 4 mL, 2.0 mmol) is heated at 65° C. for 16 hours. The volatile material is removed in vacuo and the residue is partitioned between ethyl acetate (50 mL) and water (20 mL). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×20 mL). The combined organic extract is dried and concentrated in vacuo. The crude product is purified by PTLC (hexanes/ethyl acetate 4:1) to give 6-(2,6-diethyl-phenyl)-4-methoxy-2-methyl-nicotinic acid methyl ester. 1H NMR: (CDCl3) 7.26 (m, 2H), 7.13 (d, 2H), 3.98 (s, 3H), 3.85 (s, 3H), 2.56 (s, 3H), 2.32 (m, 4H), 1.04 (t, 6H).

後処理

  1. customThe volatile material is removed in vacuo
  2. customthe residue is partitioned between ethyl acetate (50 mL) and water (20 mL)
  3. customThe organic layer is separated
  4. extractionthe aqueous layer is extracted with ethyl acetate (2×20 mL)
  5. extractionThe combined organic extract
  6. customis dried
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by PTLC (hexanes/ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-d3d1dfafbd4d4c64aa477a0fde0f8df3
出典データセット
uspto-grants-2008_03
特許番号
US07342115B2

反応ノート

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