ChemicalBook CAS DataBase List 4-tert-Butylphenyl cyclopropyl ketone

4-tert-Butylphenyl cyclopropyl ketone synthesis

4synthesis methods

Product Name:4-tert-Butylphenyl cyclopropyl ketone
CAS Number:38675-79-5
Molecular formula:C14H18O
Molecular Weight:202.29

925430-09-7
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201230-82-2 Synthesis

201230-82-2
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35779-04-5 Synthesis

35779-04-5
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38675-79-5
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Yield:38675-79-5 23 mg

Reaction Conditions:

with (η3-allyl)(N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloropalladium(II);sodium carbonate;lithium chloride in N,N-dimethyl-formamide at 80; under 760.051 Torr; for 16 h;Inert atmosphere;Sealed tube;Temperature;

Steps:

5. General procedure for the carbonylative cross-coupling

General procedure: Method A: A sealed tube equiped with a magnetic stirring bar was charged with the arylhalide (1) or (5) (1.0 equiv), sodium carbonate (2.0 equiv), anhydrous lithium chloride (2.0equiv) and (SIPr)Pd(allyl)Cl (0.05 equiv). Tricyclopropylbismuth (2a) (1.0 equiv), preparedas described above, was dissolved in anhydrous DMF (0.1 M) under argon and was addedinto the sealed tube. Carbon monoxide was bubbled in the reaction mixture for 45 seconds,then the tube was sealed and heated at 40 °C for 16 hours. The reaction mixture was cooledto room temperature, transferred in a separatory funnel containing 20 mL of an aq. sat.NaHCO3 solution and was extracted with EtOAc (3 x 20 mL). The combined organic layerswere washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated underreduced pressure. The residue was purified by flash column chromatography using theindicated solvent system to afford the desired aryl cyclopropyl ketone (3) or (6).Method B: Same as method A except that 1.5 equivalents of tricyclopropylbismuth 2ainstead of 1.0 equivalent and 0.1 equivalents of (SIPr)Pd(allyl)Cl instead of 0.05 equivalentswere used and that the reaction was heated at 80 C instead of 40 C.

References:

Benoit, Emeline;Dansereau, Julien;Gagnon, Alexandre [Synlett,2017,vol. 28,# 20,p. 2833 - 2838] Location in patent:supporting information

3972-65-4 Synthesis