Methyl morpholine oxide → 2,2-Diethyldihydro-2H-pyran-4(3H)-one

HRID 76225Notes

Reaction equation

HRID 76225 reaction equation
[CH2:1]([C:3]1([CH2:10][CH3:11])[CH2:8][CH:7]([OH:9])[CH2:6][CH2:5][O:4]1)[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:10]([C:3]1([CH2:1][CH3:2])[CH2:8][C:7](=[O:9])[CH2:6][CH2:5][O:4]1)[CH3:11]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 641051652,2-Diethyltetrahydro-2H-pyran-4-OL

Product 1

HCID 126596132,2-Diethyldihydro-2H-pyran-4(3H)-oneYield 73%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 2,2-diethyloxan-4-ol (500 mg, 3.2 mmol) in CH2Cl2 (10 ml) were added NMO (750 mg, 6.41 mmol) and 4 A molecular sieves (2 g). The solution was stirred for 30 mins and then TPAP (34 mg, 0.096 mmol) was added in one portion. The reaction was allowed to stir for 10 h. After checking the TLC, the alcohol was gone. It was filtered through a short pad of SiO2. The filtrate was concentrated and purified by normal phase SiO2 chromatography (0% to 50% EtOAc/hexanes) to give 2,2-diethyloxan-4-one (365 mg, 73%).

Workup

  1. stirringto stir for 10 h
  2. filtrationIt was filtered through a short pad of SiO2
  3. concentrationThe filtrate was concentrated
  4. custompurified by normal phase SiO2 chromatography (0% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b0a954a2383a408a8de1e658310fc18c
Source dataset
uspto-grants-2014_09
Patent number
US08835488B2

Reaction notes

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