Trifluoromethanesulfonic acid → Methyl (S)-3-benzyloxybutyrate

HRID 381230Notes

Reaction equation

HRID 381230 reaction equation
[OH:1][C@@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].ClC(Cl)(Cl)C(=N)O[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.FC(F)(F)S(O)(=O)=O>C1CCCCC1.C(Cl)Cl>[CH2:13]([O:1][C@@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 6950307Methyl 3-hydroxybutyrate, (S)-

Product 1

HCID 13967615Methyl (S)-3-benzyloxybutyrate

Reagents, catalysts & solvents 1

HCID 21916607Dichloromethane cyclohexaneSolvent2×

Procedure

Methyl (S)-(+)-3-hydroxybutyrate (17) (2.223 g, 18.82 mmol) and benzyl 2,2,2-trichloroacetimidate (4.2 mL) were dissolved into 37.5 mL of cyclohexane/methylene chloride (2:1). After the addition of 0.2 mL of trifluoromethane sulfonic acid the reaction was stirred under nitrogen for one hour. The reaction was diluted with 75 mL of cyclohexane/methylene chloride (2:1) and filtered. The organic layer was washed with 50 mL of saturated sodium bicarbonate and 50 mL of distilled water. After drying with anhydrous sodium sulfate the solution was filtered and the solvents were removed on a rotovap. The resulting solid was purified using silica gel and elution with ether/hexane (1:4).

Workup

  1. filtrationfiltered
  2. washThe organic layer was washed with 50 mL of saturated sodium bicarbonate and 50 mL of distilled water
  3. dry with materialAfter drying with anhydrous sodium sulfate the solution
  4. filtrationwas filtered
  5. customthe solvents were removed on a rotovap
  6. customThe resulting solid was purified
  7. washsilica gel and elution with ether/hexane (1:4)

Sources & evidence

ORD record
ord-2dcfd35ef9884360bb841b2fe3e22f0b
Source dataset
uspto-grants-2001_10
Patent number
US06306828B1

Reaction notes

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