Methyl triflate → 3-Methoxy-2-propionyl-pent-2-enoic acid methyl ester

HRID 1011862Notes

Reaction equation

HRID 1011862 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([C:9](=[O:12])[CH2:10][CH3:11])[C:5](=[O:8])[CH2:6][CH3:7].[C:14](=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(OC)(=O)=O>CC#N>[CH3:1][O:2][C:3](=[O:13])[C:4]([C:5](=[O:8])[CH2:6][CH3:7])=[C:9]([O:12][CH3:14])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 9526Methyl triflateHCID 10796Cesium carbonateHCID 21837307Methyl 3-oxo-2-propionylpentanoate

Product 1

HCID 866265863-Methoxy-2-propionyl-pent-2-enoic acid methyl esterYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
2 °C

Procedure

7.50 g (40.3 mmol) of 3-oxo-2-propionyl-pentanoic acid methyl ester were dissolved in 40 ml of MeCN and the mixture cooled to 2° C. While stirring, 13.26 g (40.3 mmol) of caesium carbonate were added in small portions and the reaction then warmed up to RT. 6.86 g=4.73 ml (40.3 mmol) of methyl trifluoromethanesulfonate were then added drop by drop between 22 and 25° C. After 90 min, the reaction mixture was poured into crashed ice and extracted twice with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 7.86 g of crude compound as yellow oil.

Workup

  1. customthe reaction
  2. temperaturethen warmed up to RT
  3. additionthe reaction mixture was poured
  4. extractionextracted twice with Et2O
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-332e308474d54c839d28b17135709015
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

Loading…