Lithium Hydroxide → HCID 19875375, compound

HRID 1677519Notes

Reaction equation

HRID 1677519 reaction equation
C[O:2][C:3](=[O:12])[C:4]([CH3:11])([CH3:10])[CH2:5][CH2:6][CH2:7][C:8]#[N:9].[Li+].[OH-]>O1CCCC1.CO.O>[C:8]([CH2:7][CH2:6][CH2:5][C:4]([CH3:11])([CH3:10])[C:3]([OH:12])=[O:2])#[N:9]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59540526HCID 59540526, compound

Product 1

HCID 19875375HCID 19875375, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 5-cyano-2,2-dimethyl-pentanoic acid methyl ester (4.50 g, 27 mmol) and 2 M aq. LiOH solution (40 mL, 80 mmol) in 30 mL of a 3:2:1 tetrahydrofuran/methanol/water solution was rapidly stirred overnight, then concentrated to approximately half volume. The mixture was extracted with ethyl acetate, then acidified with conc. HCl solution and extracted three times with ethyl acetate. The final three organic layers were combined and sequentially washed with sat. aq. NaHCO3 solution and sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated to afford 2.77 g (67%) of 5-cyano-2,2-dimethyl-pentanoic acid as a brown oil, which was used without further purification.

Workup

  1. concentrationconcentrated to approximately half volume
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. washsequentially washed with sat. aq. NaHCO3 solution and sat. aq. NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d6f41abb2bb463bab46b1eefc1422f6
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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