Trifluoromethanesulfonic acid → Methyl 2-hydroxy-3-phenylpropanoate

HRID 479758Notes

Reaction equation

HRID 479758 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].FC(S(O)(=O)=O)(F)F.ClC(Cl)(Cl)C(=N)O[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:19]([CH:2]([OH:3])[C:1]([O:5][CH3:6])=[O:4])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 66774Methyl GlycolateHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 516892Sodium Bicarbonate

Product 1

HCID 518800Methyl 2-hydroxy-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing methyl glycolate (2.5 mL, 32 mmol) and trifluoromethyl-sulfonic acid (150 mL) in CH2Cl2 (10 mL) was added benzyl 2,2,2-trichloro-acetimidate (7.0 mL, 37 mmol). After stirring for several min, the mixture was poured into aqueous NaHCO3 and extracted with Et2O. The organic extract was washed with saturated aqueous NaCl, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 9-17% EtOAC/Hex to afford the title compound: 1H NMR CDCl3): d 7.34 (m, 5H); 4.62 (s, 2H); 4.11 (s, 2H); 3.78 (s, 3H).

Workup

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with a solvent gradient of 9-17% EtOAC/Hex

Sources & evidence

ORD record
ord-af0467fa14d9463ab0694ddf63829b81
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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