Dimethylformamide → 2-Chloro-4-(1-pyrrolidinylmethyl)-benzaldehyde

HRID 514591ノート

反応式

HRID 514591 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[Cl:14].[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1.CCCCCC>[Cl:14][C:3]1[CH:4]=[C:5]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][C:2]=1[CH:23]=[O:24]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 58258314HCID 58258314、化合物HCID 178418339Butyllithium

生成物 1

HCID 582584922-Chloro-4-(1-pyrrolidinylmethyl)-benzaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

Reaction under N2 atmosphere. A solution of 1-[(4-bromo-3-chlorophenyl)methyl]-pyrrolidine (25.8 g, 93.96 mmol) in THF (200 ml) was stirred at −78° C. for 15 min A 2.5 M n-BuLi solution in hexane was added to the mixture over a period of 15 min. After 30 min, a solution of DMF (7.3 ml, 93.96 mmol) in THF (50 ml) was added dropwise to the mixture. The reaction temperature was allowed to rise to r.t. slowly, and the mixture was stirred overnight. The reaction was quenched by the addition of water at 0° C. The mixture was extracted with EtOAc (3×150 ml). The combined organic layer was washed with brine, dried (MgSO4), filtered and the solvent was evaporated in vacuo.

後処理

  1. customReaction under N2 atmosphere
  2. additionwas added to the mixture over a period of 15 min
  3. customto rise to r.t.
  4. customThe reaction was quenched by the addition of water at 0° C
  5. extractionThe mixture was extracted with EtOAc (3×150 ml)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-e9cfd6c7537341048d48c197ace69fb2
出典データセット
uspto-grants-2015_08
特許番号
US09107946B2

反応ノート

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