Hydrochloric Acid → 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

HRID 1429131Notes

Reaction equation

HRID 1429131 reaction equation
[OH-].[Na+].C[O:4][C:5]([CH:7]1[CH2:11][CH:10](O)[CH2:9][CH:8]1[C:13]([O:15]C)=[O:14])=[O:6].Cl>CO>[O:14]=[C:13]1[CH:8]2[CH2:9][CH:10]([CH2:11][CH:7]2[C:5]([OH:4])=[O:6])[O:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5601004-Hydroxy-cyclopentane-1,2-dicarboxylic acid, dimethyl ester

Product 1

HCID 462449653-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (1M, 74 mL, 0.074 mol) was added to a stirred solution of compound 3a (3.73 g, 0.018 mol) in methanol (105 mL) at room temperature. After 4 h, the reaction mixture was neutralized with 3M HCl, evaporated and co-evaporated with toluene several times. Pyridine (75 mL) and Ac2O (53 mL) were added and the reaction mixture was allowed to shake overnight at room temperature. The mixture was then co-evaporated with toluene and purified by flash column chromatography (ethyl acetate+1% acetic acid) which gave the title compound (2.51 g, 88%) as a yellow oil.

Workup

  1. customevaporated
  2. additionPyridine (75 mL) and Ac2O (53 mL) were added
  3. waitto shake overnight at room temperature
  4. custompurified by flash column chromatography (ethyl acetate+1% acetic acid) which

Sources & evidence

ORD record
ord-cd29ad04fccf4828ada64ad263198fd2
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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