Isopropanol → (S)-methyl 2-hydroxy-3-isopropoxypropanoate

HRID 1098107

Reaction equation

HRID 1098107 reaction equation
[O:1]1[CH2:3][C@H:2]1[C:4]([O:6][CH3:7])=[O:5].FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=[O:20].[CH3:25][CH:26](O)[CH3:27]>C(OCC)(=O)C>[OH:20][C@@H:2]([CH2:3][O:1][CH:26]([CH3:27])[CH3:25])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 2734125Magnesium trifluoromethanesulfonateHCID 10942355Methyl (2S)-2-oxiranecarboxylate

Product 1

HCID 59279510(S)-methyl 2-hydroxy-3-isopropoxypropanoateYield 302.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(S)-Methyl oxirane-2-carboxylate (2.04 g, 19.98 mmol), magnesium trifluoromethanesulfonate (1.611 g, 5.00 mmol) and propan-2-ol (1.84 mL, 24.0 mmol) in ethyl acetate (10 mL) were heated at reflux for 90 hours. The mixture was diluted with EtOAc (20 mL), filtered and evaporated. The residue was purified by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane to afford (S)-methyl 2-hydroxy-3-isopropoxypropanoate (2.45 g, 76%). 1H NMR (400 MHz, CDCl3) δ 1.13 (3H, d), 1.16 (3H, d), 3.00 (1H, d), 3.58-3.64 (1H, m), 3.68-3.74 (2H, m), 3.69-3.73 (1H, m), 3.80 (3H, s), 4.28-4.31 (1H, m)

Workup

  1. temperatureat reflux for 90 hours
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was purified by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane

Sources & evidence

ORD record
ord-4d1a56a56df94e5dabaf003a261013f7
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Linked notes

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