Ethyl bromoacetate → 5-(diphenylmethyl)-1-ethoxycarbonylmethyl-2(1H)-pyridinone

HRID 2389310ノート

反応式

HRID 2389310 の反応式
[H-].[Li+].[C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[C:3]1([CH:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][C:13](=[O:16])[N:14]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:15]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 62714Lithium hydrideHCID 227488105-(Diphenylmethyl)-2-pyridone

生成物 1

HCID 685365345-(diphenylmethyl)-1-ethoxycarbonylmethyl-2(1H)-pyridinone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of LiH (45.6 mg) in DMF (6.0 mL) was added portionwise 5-(diphenylmethyl)-2(1H)-pyridinone (500 mg) at ambient temperature and the mixture was stirred at the same temperature for 15 minutes. Ethyl bromoacetate (255 μL) was added dropwise to the mixture. The mixture was stirred at ambient temperature for 14 hours. The reaction was quenched with 1M HCl aqueous solution (10.0 mL) and the mixture was extracted with EtOAc (30 mL). The organic layer was washed successively with saturated NaHCO3 aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=3:2) to afford 5-(diphenylmethyl)-1-ethoxycarbonylmethyl-2(1H)-pyridinone (574 mg) as a colorless amorphous.

後処理

  1. stirringThe mixture was stirred at ambient temperature for 14 hours
  2. customThe reaction was quenched with 1M HCl aqueous solution (10.0 mL)
  3. extractionthe mixture was extracted with EtOAc (30 mL)
  4. washThe organic layer was washed successively with saturated NaHCO3 aqueous solution and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=3:2)

出典と根拠

ORDレコード
ord-8ed47085b7bf48baa4ff12f4f1b9173d
出典データセット
uspto-grants-2012_09
特許番号
US08273745B2

反応ノート

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