Hexane → N-[4-chloro-2-(hydroxy-pyridin-3-yl-methyl)-phenyl]-2,2-dimethyl-propionamide

HRID 495533ノート

反応式

HRID 495533 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=[O:33])[CH:27]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[C:6]([CH:32]([OH:33])[C:28]2[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=2)[CH:7]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 103713-PyridinecarboxaldehydeHCID 182511Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-HCID 178418339Butyllithium

生成物 1

HCID 22327296N-[4-chloro-2-(hydroxy-pyridin-3-yl-methyl)-phenyl]-2,2-dimethyl-propionamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

N-(4-Chloro-phenyl)-2,2-dimethyl-propionamide (3.0, 14.2 mmol) was dissolved in 15 mL THF in a dry 100 mL flask fitted with a rubber septa and nitrogen inlet and cooled to 0° C. in ice water bath for 25 minutes. A solution of 2.5M BuLi in hexane (17.0 mL, 42.6 mmol) was added and the mixture stirred for 45 minutes. To the thick yellow precipitate that formed was added a solution of pyridine-3-carboxaldehyde (3.03 g, 28.4 mmol) in 15 mL THF. The ice bath was removed and the mixture was allowed to stir at room temperature for 45 minutes and the reaction was quenched with 25 mL H2O. The mixture was transferred to a separating funnel, and the aqueous phase was discarded. The organics were dried in vacuo to yield product as an orange oil. 1H NMR (CDCl3) δ 8.85 (m, 1H) 8.54 (m, 1H) 8.42 (m, 1H) 8.10 (dd, J=8.8 Hz, 2.8 Hz, 1H) 7.50 (d, J=8.0 Hz, 1H) 7.31 (m, 1H) 7.23 (m, 1H) 7.10 (m, 1H) 5.85 (m, 1H) 1.70 (d, 1H) 1.08 (s, 9H); MS (ES) m/z=319.1 (MH)+.

後処理

  1. customfitted with a rubber septa and nitrogen inlet
  2. customTo the thick yellow precipitate that formed
  3. customThe ice bath was removed
  4. stirringto stir at room temperature for 45 minutes
  5. customthe reaction was quenched with 25 mL H2O
  6. customThe mixture was transferred to a separating funnel
  7. customThe organics were dried in vacuo
  8. customto yield product as an orange oil

出典と根拠

ORDレコード
ord-14ff8e6d9d244b96a7514e212fe31419
出典データセット
uspto-grants-2005_09
特許番号
US06939885B2

反応ノート

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