Acetic Anhydride → (3-Methyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridin-2-yl)methanol

HRID 1645528노트

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HRID 1645528 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH2:10][C:11]2([CH3:21])[O:20][CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][O:12]2)[CH:5]=[CH:4][N+:3]=1[O-].C(N(CC)CC)C.C(OC(=O)C)(=[O:32])C>>[CH3:8][C:7]1[C:2]([CH2:1][OH:32])=[N:3][CH:4]=[CH:5][C:6]=1[O:9][CH2:10][C:11]1([CH3:21])[O:20][CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13][O:12]1

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 597925822,3-Dimethyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridine 1-oxide

생성물 1

HCID 59792595(3-Methyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridin-2-yl)methanol수율 26.1%

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온도
50 °C

실험 절차

The 2,3-dimethyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridine 1-oxide (1.20 g, 3.84 mmol) obtained in the step (5d) was mixed with acetic anhydride (10 ml). To the mixture, triethylamine (0.8 ml, 5.74 mmol) was added and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was concentrated and methanol (10 ml) was added to the residue. Thereafter a 5N aqueous sodium hydroxide solution (7 ml) was added to the mixture, and stirred at room temperature for 30 minutes. To the resultant mixture, a saturated aqueous ammonium chloride solution (7 ml) was added and the pH 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 (312 mg, 26.1% yield) as a light yellow solid.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionmethanol (10 ml) was added to the residue
  3. additionThereafter a 5N aqueous sodium hydroxide solution (7 ml) was added to the mixture
  4. stirringstirred at room temperature for 30 minutes
  5. additionTo the resultant 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-b802cd18d1654eafa1033237ab196517
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124780B2

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