Toluene → Methyl 4-formyloxane-4-carboxylate

HRID 2410349Notes

Reaction equation

HRID 2410349 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 53418117Methyl 4-formyloxane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6eb22d731d7d4ba98e8c556aa252ee67
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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