Trifluoromethanesulfonic acid → Methyl 2-hydroxy-3-phenylpropanoate

HRID 479758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479758
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 518800Methyl 2-hydroxy-3-phenylpropanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-af0467fa14d9463ab0694ddf63829b81
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645989B2

Notizen zur Reaktion

Wird geladen…