5-Methyl-1,3-dioxane-5-methanol → 3-Methoxy-2-methyl-4-(5-methyl-1,3-dioxan-5-yl-methoxy)pyridine-N-oxide

HRID 1647173

반응식

HRID 1647173 반응식
[OH:1][CH2:2][C:3]1([CH3:9])[CH2:8][O:7][CH2:6][O:5][CH2:4]1.[H-].[Na+].Cl[C:13]1[CH:18]=[CH:17][N+:16]([O-:19])=[C:15]([CH3:20])[C:14]=1[O:21][CH3:22]>C1COCC1>[CH3:22][O:21][C:14]1[C:15]([CH3:20])=[N+:16]([O-:19])[CH:17]=[CH:18][C:13]=1[O:1][CH2:2][C:3]1([CH3:9])[CH2:8][O:7][CH2:6][O:5][CH2:4]1

참가 물질

5

반응물 3

HCID 142785-Methyl-1,3-dioxane-5-methanolHCID 24758Sodium hydrideHCID 5083929Pyridine, 4-chloro-3-methoxy-2-methyl-, 1-oxide

생성물 1

HCID 199264413-Methoxy-2-methyl-4-(5-methyl-1,3-dioxan-5-yl-methoxy)pyridine-N-oxide수율 24.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A deareated solution of 5-(hydroxymethyl)-5-methyl-1,3-dioxane (1.19 g, 9 mmol) in 125 ml dry THF was treated with NaH (0.79 g 55% dispersion in oil, 18 mmol) for 20 min. 4-Chloro-3-methoxy-2-methylpyridine-N-oxide (1.04 g, 6 mmol) was added and the mixture was refluxed for 26 h. Excess NaH was quenched with 10 ml of H2O and the solvent evaporated. The residue was partitioned between 150 ml CH2Cl2 and 50 ml 5% Na2CO3. The organic layer was passed through a phase separation paper and evaporated leaving 1.83 g enriched product. Chromatography (SiO2CH2Cl2 /MeOH, 95/5) afforded 0.39 g (24%) pure title compound as a tanned oil.

후처리

  1. temperaturethe mixture was refluxed for 26 h
  2. customExcess NaH was quenched with 10 ml of H2O
  3. customthe solvent evaporated
  4. customThe residue was partitioned between 150 ml CH2Cl2 and 50 ml 5% Na2CO3
  5. customThe organic layer was passed through a phase separation paper
  6. customevaporated
  7. customleaving 1.83 g

출처 및 근거

ORD 기록
ord-74b8ce39ae504535910b2f3364759b16
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05430042

연결된 노트

불러오는 중…