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

HRID 1956120노트

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HRID 1956120 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-df06ab331d7e468dabf28122026387a3
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780241

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