Dimethylformamide → 2,6-Dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

HRID 1514882노트

반응식

HRID 1514882 반응식
Br[C:2]1[C:15]([CH3:16])=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[CH3:17].[Li]CCCC.CN([CH:26]=[O:27])C>C1COCC1>[CH3:17][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:14]=[C:15]([CH3:16])[C:2]=1[CH:26]=[O:27]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 669656511-[2-(4-Bromo-3,5-dimethyl-phenoxy)-ethyl]-pyrrolidineHCID 178418339Butyllithium

생성물 1

HCID 866512592,6-Dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 1-[2-(4-bromo-3,5-dimethyl-phenoxy)-ethyl]-pyrrolidine (176 mg) in THF (5 mL) was added n-BuLi (1.36 mL, 1.0 M solution in hexane) at −78° C. The mixture was stirred at −78° C. for 30 min, allowed to warm up to −40° C. for 5 min, and then cooled down to at −78° C. After 20 min. DMF (0.24 mL) was added. The mixture was stirred at −78° C. for 30 min and then allowed to warm up to room temperature for 1 h. The reaction was quenched with saturated NH4Cl aqueous solution and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give 2,6-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde: MS (m/z) 248 (M+1).

후처리

  1. temperatureto warm up to −40° C. for 5 min
  2. temperaturecooled down to at −78° C
  3. waitAfter 20 min
  4. stirringThe mixture was stirred at −78° C. for 30 min
  5. temperatureto warm up to room temperature for 1 h
  6. customThe reaction was quenched with saturated NH4Cl aqueous solution
  7. extractionextracted with EtOAc
  8. washThe organic extracts were washed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-31873e92ec6e47d283e84029681b3008
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222248B2

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