Toluene → Methyl 4-formyloxane-4-carboxylate

HRID 2410349ノート

反応式

HRID 2410349 の反応式
[O:1]1[CH2:6][CH2:5][C:4]([C:11](OC)=[O:12])([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[H-].C1(C)C=CC=CC=1>ClCCl>[CH:11]([C:4]1([C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[O:12]

参加物

5

反応物 3

HCID 1140TolueneHCID 166653HydrideHCID 11063483Dimethyl Tetrahydropyran-4,4-dicarboxylate

生成物 1

HCID 53418117Methyl 4-formyloxane-4-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of dimethyl tetrahydro-4H-pyran-4,4-dicarboxylate (3.9 g, 19.3 mmol) in dichloromethane (38 mL) was added dropwise a 1.01 M solution of diisobutylalminium hydride in toluene (38.2 mL, 38.6 mmol) at −78° C. over 30 min period. After being stirred at this temperature for 3 h, the mixture was quenched with followed by addition of aq. ammonium chloride and 2N hydrochloric acid. The mixture was allowed to warm to room temperature and filtered through a pad of celite. The filtrate was washed with water and dried over sodium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethylacetate 5:1) to affored 2.14 g (64%) of the title compound as a colorless oil.

後処理

  1. customthe mixture was quenched
  2. additionwith followed by addition of aq. ammonium chloride and 2N hydrochloric acid
  3. filtrationfiltered through a pad of celite
  4. washThe filtrate was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customThe residual oil was purified by silica gel column chromatography (hexane/ethylacetate 5:1) to affored 2.14 g (64%) of the title compound as a colorless oil

出典と根拠

ORDレコード
ord-6eb22d731d7d4ba98e8c556aa252ee67
出典データセット
uspto-grants-2014_08
特許番号
US08816090B2

反応ノート

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