Sulfuric acid methanol → 2,4-Dimethoxy-3-hydroxy pentane

HRID 1370678Notes

Reaction equation

HRID 1370678 reaction equation
CO[Na].[CH3:4][O:5][CH:6]([CH:8]1[CH:10]([CH3:11])[O:9]1)[CH3:7].[CH3:12][OH:13].OS(O)(=O)=O>CO>[CH3:12][O:13][CH:10]([CH:8]([OH:9])[CH:6]([O:5][CH3:4])[CH3:7])[CH3:11]

Participants

5

Reactant 3

HCID 18363649Sulfuric acid methanolHCID 186264262-(1-Methoxyethyl)-3-methyl oxiraneHCID 178418582HCID 178418582, compound

Product 1

HCID 224955082,4-Dimethoxy-3-hydroxy pentane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Pentanone was brominated to get 2,4-dibromo-3-pentanone(1.2.4.11) using conventional methods. The dibromoketone was reduced with BH3*THF to the corresponding alcohol(1.2.4.15). This compound was reacted with MeONa in methanol to yield 2-(1-bromoethyl)-3-methyl oxirane(1.2.4.13) which after reaction with MeOH/H2SO4 gave 2-bromo-3-hydroxy-4-methoxy pentane(1.2.4.38). This intermediate was reacted again with MeONa in methanol and the resulting 2-(1-methoxyethyl)-3-methyl oxirane(1.2.4.22) was reacted again with MeOH/H2SO4 to yield 2,4-dimethoxy-3-hydroxy pentane(1.2.4.39). After oxidation with CrO3/Py in methylenechloride the resulting ketone was reacted with trimethylsulfoxonium iodide to give the title compound (1.2.4.37).

Sources & evidence

ORD record
ord-67d68b6651ec4281be89bae8adc631d6
Source dataset
uspto-grants-2003_06
Patent number
US06583182B1

Reaction notes

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