Sodium Hydroxide → HCID 66902185, compound

HRID 2242305Notes

Reaction equation

HRID 2242305 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]2[CH:3]1[C@H:4]2[C:8]([O:10]CC)=[O:9].[OH-].[Na+]>C(O)C>[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]2[CH:3]1[C@H:4]2[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66902515HCID 66902515, compound

Product 1

HCID 66902185HCID 66902185, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude ethyl (6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylate (30.2 g, 180 mmol, uncorrected) in 30 mL of ethanol at room temperature is added 89 mL (178 mmol) of 2N sodium hydroxide. Upon stirring for 80 minutes, the reaction mixture is washed with tert-butyl methyl ether (1×90 mL) and the aqueous layer is treated with conc. hydrochloric acid (18 mL) to reach a pH=1.0. The mixture is treated with 15 g of sodium chloride followed by washing with ethyl acetate (3×90 mL). The combined organic extracts are dried (Na2SO4), filtered, and concentrated in vacuo to give 23.8 g (94%, uncorrected) of the title compound as an off-white solid.

Workup

  1. washthe reaction mixture is washed with tert-butyl methyl ether (1×90 mL)
  2. additionthe aqueous layer is treated with conc. hydrochloric acid (18 mL)
  3. additionThe mixture is treated with 15 g of sodium chloride
  4. washby washing with ethyl acetate (3×90 mL)
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a0b20126c254cfc988e5ed0f7ae6b47
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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