Pyridine N-Oxide → Methyl 3,3-dimethyl-5-oxovalerate

HRID 1290298

反応式

HRID 1290298 の反応式
Br[CH2:2][CH2:3][C:4]([CH3:11])([CH3:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[N+]1([O-:18])C=CC=CC=1.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[NH4+].[NH4+]>C1(C)C=CC=CC=1.O>[CH3:10][C:4]([CH3:11])([CH2:3][CH:2]=[O:18])[CH2:5][C:6]([O:8][CH3:9])=[O:7]

参加物

7

反応物 4

HCID 12753Pyridine N-OxideHCID 516892Sodium BicarbonateHCID 517111Ammonium CarbonateHCID 15276782Methyl 5-bromo-3,3-dimethylpentanoate

生成物 1

HCID 3018723Methyl 3,3-dimethyl-5-oxovalerate収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

A mixture of methyl 5-bromo-3,3-dimethylpentanoate (5.0 g), pyridine-N-oxide (4.49 g), sodium bicarbonate (3.77 g) and toluene (30 cm3) was heated at the reflux temperature with vigorous agitation for a period of 14 hours. After cooling the mixture to the ambient temperature, water (20 cm3), saturated ammonium carbonate solution (20 cm3) and toluene (50 cm3) were added and the aqueous phase separated and extracted with toluene (3×75 cm3). The toluene extracts were added to the main organic phase and the whole dried over anhydrous magnesium sulphate concentrated by evaporation of the more volatile components under reduced pressure. The residual liquid was purified by Kugelrohr distillation (130° C./water pump pressure) to give methyl 3,3-dimethyl-5-oxopentanoate in 63% yield.

後処理

  1. temperaturewas heated at the reflux temperature with vigorous agitation for a period of 14 hours
  2. additionwere added
  3. customthe aqueous phase separated
  4. extractionextracted with toluene (3×75 cm3)
  5. additionThe toluene extracts were added to the main organic phase
  6. dry with materialthe whole dried over anhydrous magnesium sulphate
  7. concentrationconcentrated by evaporation of the more volatile components under reduced pressure
  8. distillationThe residual liquid was purified by Kugelrohr distillation (130° C./water pump pressure)

出典と根拠

ORDレコード
ord-9f168e7594f146d59b75304cfdc50861
出典データセット
uspto-grants-1998_05
特許番号
US05750769

関連ノート

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