Hydrochloric Acid → 1-Butylcyclobutanecarboxylic Acid

HRID 1868435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1868435
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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 133895511-Butylcyclobutanecarboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 86600160Heptane tetrahydrofuran benzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-bfd8c2a08d5d436b83aae5bcda536170
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07635713B2

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