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

HRID 514591노트

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HRID 514591 반응식
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]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 58258314HCID 58258314, 화합물HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9cfd6c7537341048d48c197ace69fb2
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09107946B2

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