Hydrochloric Acid → 1-Butylcyclobutanecarboxylic Acid

HRID 1868435Notes

Reaction equation

HRID 1868435 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH:9]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]1.[CH2:16](I)[CH2:17][CH2:18][CH3:19].Cl>CCCCCCC.O1CCCC1.C1C=CC=CC=1.C1COCC1>[CH2:16]([C:9]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]1)[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 19494Cyclobutanecarboxylic acidHCID 2724682Lithium diisopropylamide2×

Product 1

HCID 133895511-Butylcyclobutanecarboxylic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 86600160Heptane tetrahydrofuran benzeneSolvent

Procedure

A solution of lithium di-isopropylamide (100 mL, 2.0 M, 200 mmol) in heptane/tetrahydrofuran/benzene was diluted with 100 mL of anhydrous THF. To the LDA solution at 0° C. was added dropwise 10 g (100 mmol) of cyclobutanecarboxylic acid in 15 mL of anhydrous THF over 20 minutes under Argon. The mixture was sired at room temperature for 3 hours. To the reaction mixture was added 11.4 mL (100 mmol) of butyl iodide at 0° C. The reaction mixture was warmed to RT and stirred overnight. HCl (2N) was used to adjust the pH to 2˜3. The mixture was extracted with EtOAc (3×200 mL). The combined organic phase was washed with 100 mL of brine, dried (MgSO4) and concentrated. Thus obtained crude product was used directly for next step.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×200 mL)
  2. washThe combined organic phase was washed with 100 mL of brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThus obtained crude product

Sources & evidence

ORD record
ord-bfd8c2a08d5d436b83aae5bcda536170
Source dataset
uspto-grants-2009_12
Patent number
US07635713B2

Reaction notes

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