Sodium Hydroxide → ethyl N-(diphenylmethylidene)-3-(2-methoxy-3-pyridinyl)alaninate

HRID 1972652노트

반응식

HRID 1972652 반응식
Br[CH2:2][C:3]1[C:4]([O:9][CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[C:11]1([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O1CCCC1.O>[C:11]1([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18][C@H:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:2][C:3]2[C:4]([O:9][CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 575745123-(Bromomethyl)-2-methoxypyridine

생성물 1

HCID 86670427ethyl N-(diphenylmethylidene)-3-(2-methoxy-3-pyridinyl)alaninate수율 71.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a 100-mL round-bottomed flask were added 3-(bromomethyl)-2-methoxypyridine (1.10 g, 5.44 mmol), ethyl N-(diphenylmethylene)glycinate (1.46 g, 5.44 mmol, Acros, N.J.) and 5N sodium hydroxide (5.44 mL, 27.2 mmol) in tetrahydrofuran (30 mL). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated NaCl (20 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give ethyl N-(diphenylmethylidene)-3-(2-methoxy-3-pyridinyl)alaninate (1.52 g) as viscous oil.

후처리

  1. extractionextracted with EtOAc (2×50 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaCl (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo
  7. customto give the crude material as light-yellow oil
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 20% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-2b0859d8251b438bb91488379ce4442b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431563B2

반응 노트

불러오는 중…