Hydrochloric Acid → 1-Butylcyclobutanecarboxylic Acid

HRID 28782

Reaktionsgleichung

Reaktionsgleichung von HRID 28782
[Li+].CC([N-]C(C)C)C.[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>C1COCC1.CCCCCCC.C(C1C=CC=CC=1)C.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 diisopropylamide

Produkt 1

HCID 133895511-Butylcyclobutanecarboxylic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 22742125Tetrahydrofuran heptane ethylbenzolLösungsmittel

Versuchsvorschrift

To a solution of LDA (30 mL, 2.0M, 60 mmol) in THF/heptane/ethylbenzene and anhydrous THF (30 mL) at 0° C. was added cyclobutane carboxylic acid (3.0 g, 30 mmol) dropwise. After addition was complete, the cold bath was removed, the reaction mixture was stirred at room temperature for 2 hr. Neat n-BuI (3.41 mL, 30 mmol) was added dropwise at room temperature. The mixture was stirred over night. To the mixture was added 2N HCl and the mixture was extracted with ethyl acetate. The combined organic phase was washed with water and brine to afford the title compound as a light yellow oil (quantitative), which was used in the next step without purification.

Aufarbeitung

  1. additionAfter addition
  2. customthe cold bath was removed
  3. stirringThe mixture was stirred over night
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined organic phase was washed with water and brine

Quellen und Nachweise

ORD-Eintrag
ord-4543cd007d8f4a4d963bcad71a899e4c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419999B2

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