Dimethyl Sulfoxide → 4-(Azidopropoxy)-2,6-diformyl-pyridine

HRID 1956120ノート

反応式

HRID 1956120 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([CH2:24][OH:25])[N:21]=[C:20]([CH2:26][OH:27])[CH:19]=1)=[N+:12]=[N-:13].C(N(CC)CC)C>C(Cl)Cl>[N:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([CH:24]=[O:25])[N:21]=[C:20]([CH:26]=[O:27])[CH:19]=1)=[N+:12]=[N-:13]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 543426824-(3-Azidopropoxy)-2,6-dihydroxymethylpyridine

生成物 1

HCID 223237004-(Azidopropoxy)-2,6-diformyl-pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

DMSO (1.21 mL, 17.1 mmol) was diluted with CH2Cl2 (approximately 25 mL) and cooled to -78° C. Oxalyl chloride (0.745 mL, 8.45 mmol) was added dropwise and the reaction mixture was stirred for 15 minutes. 4-(3-azidopropoxy)-2,6-dihydroxymethylpyridine (1 g, 4.27 mmol) dissolved in CH2Cl2 (10 mL) was added slowly to the cooled reaction mixture. After 0.5 hour triethylamine (2.77 mL, 19.70 mmol) was added dropwise to the reaction mixture. The dry ice/acetone bath was removed and the reaction mixture was warmed to room temperature for approximately 40 minutes. The reaction mixture was partitioned between CH2Cl2 and water and extracted several times with CH2Cl2. The CH2Cl2 layers were combined, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by silica gel flash column chromatography to give the title compound. 1H NMR (DMSO) δ 2.02 (m, 2H, CH2), 3.52 (t, 2H, CH2), 4.31 (t, 2H, CH2), 7.64 (s, 2H, 2×Ar), 10.01 (s ,2H, CHO). 13C NMR (DMSO) δ 27.61 (CH2), 47.40 (CH2), 66.22 (CH2), 111.58 (Ar), 154.40 (quaternary, Ar), 166,50 (quaternary, Ar), 192.44 (CHO).

後処理

  1. additionwas added slowly to the cooled reaction mixture
  2. customThe dry ice/acetone bath was removed
  3. temperaturethe reaction mixture was warmed to room temperature for approximately 40 minutes
  4. customThe reaction mixture was partitioned between CH2Cl2 and water
  5. extractionextracted several times with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-df06ab331d7e468dabf28122026387a3
出典データセット
uspto-grants-1998_07
特許番号
US05780241

反応ノート

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