Toluene → Methyl 4-formyloxane-4-carboxylate

HRID 2410349노트

반응식

HRID 2410349 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 53418117Methyl 4-formyloxane-4-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6eb22d731d7d4ba98e8c556aa252ee67
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816090B2

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