Methyl formate → 3-Oxo-cyclopentanecarboxylic acid methyl ester

HRID 375994

反応式

HRID 375994 の反応式
CO[CH:3]([O:6][CH3:7])[O:4]C.[O:8]=[C:9]1[CH2:13][CH2:12][CH:11](C(O)=O)[CH2:10]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.COC=O.C[O-].[Na+]>CO>[CH3:7][O:6][C:3]([CH:11]1[CH2:12][CH2:13][C:9](=[O:8])[CH2:10]1)=[O:4]

参加物

7

反応物 5

HCID 7865Methyl formateHCID 9005Trimethyl orthoformateHCID 2277983-Oxocyclopentanecarboxylic acidHCID 521998p-Toluenesulfonic acid monohydrateHCID 10942334Sodium Methoxide

生成物 1

HCID 2376403-Oxo-cyclopentanecarboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
10 °C

実験手順

318.36 g (3 mol) of trimethylorthoformate are added gradually to a solution of 128.2 g (1 mol) of nonracemic 3-oxocyclopentanecarboxylic acid and 11.4 g (0.06 mol) of p-toluene sulfonic acid hydrate in 380 ml of methanol within 5-10 minutes while stirring, The mixture is heated and during 25 minutes a mixture of formic acid methyl ester and methanol is distilled off (about 185 g of distillate), Thereafter 29 g of 30% sodium methylate solution (0.16 mol) are added and the reaction mixture is kept boiling under reflux for 2 hours; methanol is distilled off, the residue cooled to 10° C. and dissolved by adding 230 ml of methylene chloride and 200 ml of water. By adding 5% sulfuric acid the mixture is adjusted to pH 1.4 and stirred at 10° C. for 30 minutes. The methylene chloride phase is separated and the aqueous phase extracted again with 100 ml of methylene chloride. The combined organic phases are stirred with 50 ml of water, separated and the solvent is distilled off in vacuo. The residue is fractionated in vacuo.

後処理

  1. temperatureThe mixture is heated and during 25 minutes
  2. distillationis distilled off (about 185 g of distillate)
  3. temperatureunder reflux for 2 hours
  4. distillationmethanol is distilled off
  5. dissolutiondissolved
  6. additionby adding 230 ml of methylene chloride and 200 ml of water
  7. additionBy adding 5% sulfuric acid the mixture
  8. stirringstirred at 10° C. for 30 minutes
  9. customThe methylene chloride phase is separated
  10. extractionthe aqueous phase extracted again with 100 ml of methylene chloride
  11. stirringThe combined organic phases are stirred with 50 ml of water
  12. customseparated
  13. distillationthe solvent is distilled off in vacuo

出典と根拠

ORDレコード
ord-c7e2963c623b4c9b8cea55662fcbef8f
出典データセット
uspto-grants-1996_01
特許番号
US05488136

関連ノート

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