5-(Benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde → 3-(benzyloxy)-5-bromo-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one

HRID 625970노트

반응식

HRID 625970 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([CH:17]=[O:18])=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([Mg]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([CH:17]([OH:18])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 866754905-(Benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehydeHCID 178418336HCID 178418336, 화합물

생성물 1

HCID 674201833-(benzyloxy)-5-bromo-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one수율 71.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a 0° C. solution of 5-(benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde (1.09 g, 3.38 mmol) in 34 mL THF was added benzylmagnesium chloride (2.55 g, 3.38 mmol) dropwise. The mixture was allowed to stir at 0° C. for 1 h. After warming to room temperature, volatiles were removed under reduced pressure. The resulting residue was partitioned between dilute aqueous hydrochloric acid and ethyl acetate. The aqueous layer was removed and discarded, and the organic layer was collected, dried over anhydrous magnesium sulfate and purified by silica gel chromatography to afford 3-(benzyloxy)-5-bromo-6-(1-hydroxy-2-phenylethyl)-1-methylpyridin-2(1H)-one (1 g, 2.41 mmol, 71% yield). ES-MS (M+H)+=415.

후처리

  1. temperatureAfter warming to room temperature
  2. customvolatiles were removed under reduced pressure
  3. customThe resulting residue was partitioned between dilute aqueous hydrochloric acid and ethyl acetate
  4. customThe aqueous layer was removed
  5. customthe organic layer was collected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-c6e67bc23ae4458f82269afdb6eeba43
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309199B2

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