Hydrochloric Acid → (2S)-5-oxooxolane-2-carboxylic acid

HRID 2068177Notes

Reaction equation

HRID 2068177 reaction equation
N[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].Cl.N([O-])=O.[Na+]>O.CCOC(C)=O>[O:9]=[C:8]1[O:10][C@H:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 33032L-Glutamic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 636468(2S)-5-oxooxolane-2-carboxylic acidYield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of L-glutamic acid (10.07 g, 0.068 mol, J&K CHEMICA) in 20 ml of concd. HCl and 40 mL H2O was added a solution of NaNO2 (7.0 g, 0.102 mol, Shantou Xilong chemical factory) in H2O (20 mL) slowly at −5° C. The mixture was continued to stir for 12 hrs at room temperature. The reaction mixture was evaporated in vacuo below 50° C. to give yellow oil, which was dissolved in EtOAc. The solid formed was filtered and washed with EtOAc. The filtrate and washing solution were combined, dried over Na2SO4. The solvent was concentrated in vacuo to give (S)-tetrahydro-5-oxofuran-2-carboxylic acid as pale yellow oil (8.1 g, 91.6%)1.

Workup

  1. customThe reaction mixture was evaporated in vacuo below 50° C.
  2. customto give yellow oil, which
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with EtOAc
  6. washThe filtrate and washing solution
  7. dry with materialdried over Na2SO4
  8. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-04ee6702f9ba4ea9805724e95d34db93
Source dataset
uspto-grants-2012_10
Patent number
US08293897B2

Reaction notes

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