Acetic Anhydride → (4-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methanol

HRID 1645522노트

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HRID 1645522 반응식
[CH2:1]([C:3]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N+:19]([O-])=[C:18]([CH3:23])[C:17]=2[CH3:24])[O:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][O:4]1)[CH3:2].C(N(CC)CC)C.C(OC(=O)C)(=[O:34])C>>[CH2:1]([C:3]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([CH2:23][OH:34])[C:17]=2[CH3:24])[O:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][O:4]1)[CH3:2]

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 597925064-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-2,3-dimethylpyridine 1-oxide

생성물 1

HCID 59792375(4-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methanol수율 59.6%

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온도
50 °C

실험 절차

The 4-(2-(8-ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-2,3-dimethylpyridine 1-oxide (947 mg, 2.79 mmol) obtained in the step (4f) was mixed with acetic anhydride (10 ml). To the mixture, triethylamine (0.6 ml, 4.3 mmol) was added and stirred at 50° C. for 2 hours. The reaction mixture was concentrated and methanol (10 ml) was added to the residue and thereafter, a 5N aqueous sodium hydroxide solution (7 ml) was added and stirred at room temperature for one hour. To the mixture, a saturated aqueous ammonium chloride solution (7 ml) was added and the pH of the resultant solution was adjusted to about 10. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with a 2N aqueous sodium hydroxide solution, water, and a saline solution, dried over anhydrous sodium sulfate, and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol=1/0-4/1 gradient) and a desired fraction(s) was concentrated to obtain the title compound (564 mg, yield: 59.6%) as a light yellow solid.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionmethanol (10 ml) was added to the residue
  3. additiona 5N aqueous sodium hydroxide solution (7 ml) was added
  4. stirringstirred at room temperature for one hour
  5. additionTo the mixture, a saturated aqueous ammonium chloride solution (7 ml) was added
  6. additionThe reaction mixture was diluted with ethyl acetate
  7. washthe organic layer was washed with a 2N aqueous sodium hydroxide solution, water
  8. dry with materiala saline solution, dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe obtained crude product
  11. customwas purified by silica gel column chromatography (elution solvent: ethyl acetate/methanol=1/0-4/1 gradient)
  12. concentrationa desired fraction(s) was concentrated

출처 및 근거

ORD 기록
ord-bb0e93aec87340ecbf3363501c1c8c9e
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124780B2

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