Methyl formate → 4-Ethoxy-6-(trifluoromethyl)pyrimidine-5-carbaldehyde

HRID 254219ノート

反応式

HRID 254219 の反応式
Br[C:2]1[C:3]([O:12][CH2:13][CH3:14])=[N:4][CH:5]=[N:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C([Li])CCC.[CH:20](OC)=[O:21].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:13]([O:12][C:3]1[C:2]([CH:20]=[O:21])=[C:7]([C:8]([F:11])([F:10])[F:9])[N:6]=[CH:5][N:4]=1)[CH3:14]

参加物

7

反応物 4

HCID 7865Methyl formateHCID 25517Ammonium ChlorideHCID 178628775-Bromo-4-ethoxy-6-trifluoromethylpyrimidineHCID 178418339Butyllithium

生成物 1

HCID 178628784-Ethoxy-6-(trifluoromethyl)pyrimidine-5-carbaldehyde収率 81.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A solution of 5.76 g (21.3 mmoles) of 5-bromo-4-ethoxy-6-trifluoromethylpyrimidine dissolved in 250 ml of tetrahydrofuran was cooled to −78° C. Thereinto was dropwise added 22.6 ml of a 1.6 M hexane solution containing 36.1 mM of n-butyl lithium. The mixture was stirred for 40 minutes. Thereto was added 2.7 g (45.1 mmoles) of methyl formate. The mixture was stirred for 1.5 hours to give rise to a reaction. After the completion of the reaction, an aqueous ammonium chloride solution was added and extraction with ether was conducted. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate mixed solvent) to obtain 3.82 g (yield: 81.6%) of 4-ethoxy-6-trifluoromethylpyrimidine-5-carboaldehyde.

後処理

  1. stirringThe mixture was stirred for 1.5 hours
  2. customto give rise
  3. customto a reaction
  4. customAfter the completion of the reaction
  5. extractionextraction with ether
  6. washThe resulting organic layer was washed with an aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to reduced pressure distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate mixed solvent)

出典と根拠

ORDレコード
ord-01c14bba01f0430f82fdd1b7ba0c7b21
出典データセット
uspto-grants-2011_01
特許番号
US07875606B2

反応ノート

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