2-Chloro-5-nitropyridine → HCID 67235239、化合物

HRID 1505323ノート

反応式

HRID 1505323 の反応式
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:3].CC([O-])(C)C.[K+].Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1>CS(C)=O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:11][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:1]

参加物

5

反応物 3

HCID 783082-Chloro-5-nitropyridineHCID 2353733-(propan-2-yloxy)phenol2 回HCID 23665647Potassium tert-butoxide

生成物 1

HCID 67235239HCID 67235239、化合物収率 81.5%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
20 °C

実験手順

To a solution of 3-[(1-methylethyl)oxy]phenol (Intermediate 27, 456 mg) in DMSO (8 mL) was added t-BuOK (336 mg, 3 mmol, Acros). The reaction mixture was stirred at 20° C. for 30 minutes. 2-chloro-5-nitropyridine (474 mg, 3 mmol, Aldrich) was added and the resulting mixture was stirred at 120° C. for 2 hours. The reaction mixture was cooled to room temperature, poured into ice-water (50 mL) and extracted with dichloromethane (3 times 50 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated. The residue was purified by column chromatography on silica gel eluting with (PE:EtOAc=50:1) to afford the title compound as a light yellow solid (670 mg).

後処理

  1. stirringthe resulting mixture was stirred at 120° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with dichloromethane (3 times 50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with (PE:EtOAc=50:1)

出典と根拠

ORDレコード
ord-1a2912d2fcd04b9dbbe2532c5a604279
出典データセット
uspto-grants-2015_12
特許番号
US09216967B2

反応ノート

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