3-[(2-Methoxyethoxy)methoxy]benzaldehyde → 1-(2-Methoxyethoxy)-methoxy-3-(2-quinolin-2-yl-vinyl)-benzene

HRID 892144노트

반응식

HRID 892144 반응식
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)C=CC=CC=1.C([Li])CCC.[CH3:37][O:38][CH2:39][CH2:40][O:41][CH2:42][O:43][C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][CH:51]=1)[CH:47]=O>C1COCC1>[CH3:37][O:38][CH2:39][CH2:40][O:41][CH2:42][O:43][C:44]1[CH:51]=[CH:50][CH:49]=[C:46]([CH:47]=[CH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:45]=1

참가 물질

5

반응물 3

HCID 157551753-[(2-Methoxyethoxy)methoxy]benzaldehydeHCID 22241267Triphenyl[(quinolin-2-yl)methyl]phosphanium chlorideHCID 178418339Butyllithium

생성물 1

HCID 544075821-(2-Methoxyethoxy)-methoxy-3-(2-quinolin-2-yl-vinyl)-benzene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a cooled (−78° C.) suspension of triphenyl-(quinolin-2-yl-methyl)-phosphonium chloride (1.76 g, 4 mmol, example 17) in THF (24 mL) is added, dropwise, n-butyl lithium solution (1.7 mL, 2.5 M in hexanes). The resulting mixture is stirred for 30 min. then a solution of 3-[(2-methoxyethoxy)-methoxy]-benzaldehyde (756 mg, 3.6 mmol, example 8a) in THF (3 mL) is added. This mixture is stirred for 30 min then the cold bath removed and stirring continued for 2 h. The reaction mixture is then diluted with ethyl acetate, washed with sat. ammonium acetate solution and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 40% ethyl acetate in hexanes) to give the title compound as an oil. MS (ESI) 336 (M+H)+.

후처리

  1. temperatureTo a cooled
  2. additionis added
  3. stirringThis mixture is stirred for 30 min
  4. customthe cold bath removed
  5. stirringstirring
  6. waitcontinued for 2 h
  7. additionThe reaction mixture is then diluted with ethyl acetate
  8. washwashed with sat. ammonium acetate solution and brine
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated
  11. customThe residue is purified by flash chromatography (silica, 40% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-1f4301884b474332aafc444fae97cc31
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005440B1

반응 노트

불러오는 중…