Chloroform → Ethyl 5-butoxy-1,3-oxazole-2-carboxylate

HRID 1817300ノート

反応式

HRID 1817300 の反応式
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:15]([O:17][C:18](=[O:30])[C:19]([NH:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])=O)[CH3:16].CCOC(C)=O.C(Cl)(Cl)Cl>CC#N.[Cl-].[Na+].O>[CH2:26]([O:25][C:23]1[O:24][C:19]([C:18]([O:17][CH2:15][CH3:16])=[O:30])=[N:21][CH:22]=1)[CH2:27][CH2:28][CH3:29]

参加物

7

反応物 4

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 14812Phosphorus oxide (P4O10)HCID 69643286butyl N-[ethoxy(oxo)acetyl]glycinate

生成物 1

HCID 66996945Ethyl 5-butoxy-1,3-oxazole-2-carboxylate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
50 °C

実験手順

A suspension of P2O5 (22 g, 155.6 mmol) in CH3CN (50 mL) under nitrogen was warmed to 50° C. and treated with butyl N-[ethoxy(oxo)acetyl]glycinate (6 g, 25.9 mmol) dissolved in 10 mL CH3CN. The mixture was heated to 65° C. for 1.5 hours, then cooled in an ice bath. Ice and brine were added to the reaction mixture, then EtOAc was added and the mixture transferred to a separatory funnel. CHCl3 was added to dissolve solids and the organic layer was isolated. The aqueous layer was washed repeatedly with CHCl3 and EtOAc, the organic layers were combined and dried with Na2SO4, then concentrated. The residue was chromatographed on silica eluting with a gradient of 0-30% EtOAc/Hexanes to give the product as a clear, colorless oil.

後処理

  1. temperatureThe mixture was heated to 65° C. for 1.5 hours
  2. temperaturecooled in an ice bath
  3. customthe mixture transferred to a separatory funnel
  4. dissolutionto dissolve solids
  5. customthe organic layer was isolated
  6. washThe aqueous layer was washed repeatedly with CHCl3 and EtOAc
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica eluting with a gradient of 0-30% EtOAc/Hexanes
  10. customto give the product as a clear, colorless oil

出典と根拠

ORDレコード
ord-f2dc169bf52842899053df8afcd8fa41
出典データセット
uspto-grants-2009_10
特許番号
US07598264B2

反応ノート

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