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

HRID 1514882ノート

反応式

HRID 1514882 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-31873e92ec6e47d283e84029681b3008
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

反応ノート

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