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

HRID 363730Notes

Reaction equation

HRID 363730 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). ##STR42## 1.2.5 Phosphite and Alkyl Phosphonate Esters.

Sources & evidence

ORD record
ord-34b7109a97d24952bd98cd6b4e4c4907
Source dataset
uspto-grants-1999_02
Patent number
US05874573

Reaction notes

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