Allyl bromide → Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

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Reaktionsgleichung

C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[C:21]([O:25][C:26]([CH:28]1[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(Br)C=C.[Cl-].[NH4+]>C1COCC1>[C:21]([O:25][C:26]([C:28]1([CH2:7][CH:5]=[CH2:6])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Lithium diisopropyl amide was generated from 7.5 g (58.1 mmol) diisopropyl amine and 23.2 mL of 2.5 M n-butyl lithium in 200 mL THF at 0° C. under nitrogen. After stirring for 30 minutes at 0° C. the solution was taken to −78° C. where 7.5 g (52.8 mmol) of cyclopropanecarboxylic acid tert-butyl ester in 30 mL of THF was added dropwise over 5 min. After 4 h 12.8 g (106 mmol) of allyl bromide in 30 mL THF was added drop-wise over 10 min. to the clear golden solution. The reaction was allowed to slowly warm to room temperature. After 19 hours the reaction was poured into aqueous saturated ammonium chloride solution, extracted with ether, dried and concentrated to deliver an oil which was purified via Kugelrohr distillation (approx. 20 mm Hg; 60–75° C. oven) to deliver 5.4 g (56%) of the desired product as a clear colorless oil.

Aufarbeitung

customwas taken to −78° C.
additionwas added dropwise over 5 min
temperatureto slowly warm to room temperature
extractionextracted with ether
customdried
concentrationconcentrated
distillationwas purified via Kugelrohr distillation (approx. 20 mm Hg; 60–75° C. oven)

Quellen und Nachweise

ORD-Eintrag: ord-7284de14c382437f96f2230bc0cfaead
Quelldatensatz: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07186724B2

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