Imidazole → 2-((Tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine

HRID 1811579ノート

反応式

HRID 1811579 の反応式
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([CH2:11][OH:12])[CH:3]=1.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14].N1C=CN=C1.O>C(Cl)Cl>[Si:17]([O:12][CH2:11][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 58671581(4-Methyl-5-nitropyridin-2-yl)methanol

生成物 1

HCID 586715992-((Tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of (4-methyl-5-nitropyridin-2-yl)methanol (1.2 g, 7.1 mmol) in 5 mL of CH2Cl2, were added tert-butylchlorodiphenylsilane (2.0 g, 7.1 mmol) and imidazole (0.049 g, 0.71 mmol) at an ambient temperature. The reaction was stirred at 25° C. for 2 hrs. The reaction was poured into H2O, extracted with ethyl acetate, and dried over MgSO4. The ethyl acetate was concentrated under vacuum and purified over SiO2 to afford the desired compound 2-((tert-butyldiphenylsilyloxy)methyl)-4-methyl-5-nitropyridine in 90% (2.6 g). 1HNMR (CDCl3, 400 MHz) δ 1.12 (s, 9H), 2.78 (s, 3H), 4.85 (s, 2H), 7.21 (s, 1H), 7.24˜7.89 (m, 10H), 9.15 (s, 1H).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationThe ethyl acetate was concentrated under vacuum
  4. custompurified over SiO2

出典と根拠

ORDレコード
ord-3f01225409f84ae787ff99db1b4dc9ae
出典データセット
uspto-grants-2013_01
特許番号
US08362248B2

反応ノート

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