Hydrochloric Acid → 1-(Cyclopropylmethyl)cyclobutane-1-carboxylic acid

HRID 2057159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057159
[Li+].CC([N-]C(C)C)C.[CH:9]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]1.BrC[CH2:18][CH:19]1[CH2:21][CH2:20]1.Cl>C1COCC1>[CH:19]1([CH2:18][C:9]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]2)[CH2:21][CH2:20]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 19494Cyclobutanecarboxylic acidHCID 2724682Lithium diisopropylamideHCID 22636989(2-Bromoethyl)cyclopropane

Produkt 1

HCID 450847861-(Cyclopropylmethyl)cyclobutane-1-carboxylic acidAusbeute 124,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of LDA (100 ml, 2.0 M THF solution) in THF (100 ml) was added dropwise over a period of 20 minutes at 0° C., a solution of cyclobutane carboxylic acid (10 g, 0.1 mol) in THF (15 ml). The resulting mixture was stirred at RT for 2 h then bromoethyl cyclopropane (15 g, 0.11 mol) was added dropwise and the mixture was stirred at RT overnight. To the reaction mixture was added 2N HCl and the mixture was extracted with EtOAc. The organic layer was washed with water and brine to afford the title compound as light yellow oil (19.2 g), which was used in the next step without purification.

Aufarbeitung

  1. stirringthe mixture was stirred at RT overnight
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with water and brine

Quellen und Nachweise

ORD-Eintrag
ord-21d0b11f86f348a1ac71e5808082acb6
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335680B2

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