Sodium Hydroxide → 2-Cyano-2-cyclopropylacetic acid

HRID 1946248Notes

Reaction equation

HRID 1946248 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:13])[CH:7]([C:11]#[N:12])[CH:8]1[CH2:10][CH2:9]1)C>C1COCC1>[C:11]([CH:7]([CH:8]1[CH2:10][CH2:9]1)[C:6]([OH:13])=[O:5])#[N:12]

Participants

4

Conditions

Temperature
25 °C

Procedure

IN NaOH (3.26 ml, 3.26 mmol) was added to a solution of cyano-cyclopropyl-acetic acid ethyl ester (0.5 g, 3.26 mmol) in THF (15 ml). After 4 hours stirring at 25° C., the reaction mixture was evaporated in vacuo, re-dissolved in water (20 ml) and neutralized by the addition of 1N HCl solution (3.26 ml). This mixture was then extracted with EtOAc (3×20 ml) and the combined, dried (Na2SO4) organics evaporated in vacuo to give impure cyano-cyclopropyl-acetic acid as a clear oil. This material was used without any further purification in the preparation of Example 4B.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionre-dissolved in water (20 ml)
  3. additionneutralized by the addition of 1N HCl solution (3.26 ml)
  4. extractionThis mixture was then extracted with EtOAc (3×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customorganics evaporated in vacuo

Sources & evidence

ORD record
ord-f20027fce5f64509b77f8a4d0990225d
Source dataset
uspto-grants-2013_03
Patent number
US08399442B2

Reaction notes

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