Hantzsch ester → 3-(4-chlorophenyl)-1-phenylpropan-1-one

HRID 1402873Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Silica gel (5.26 g) was added to a solution of 3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (0.636 g) and 3,5-bis(ethoxycarbonyl)-1,4-dihydro-2,6-dimethylpyridine (1 g) in toluene (20 ml). The slurry was stirred at 70° C. in the dark for 17 h. After removal of the solvent the residue was purified by flash chromatography on silica gel (petrol ether/ethyl acetate) to provide 3-(4-chlorophenyl)-1-phenylpropan-1-one (0.49 g) as colourless solid.

Workup

customAfter removal of the solvent the residue
customwas purified by flash chromatography on silica gel (petrol ether/ethyl acetate)

Sources & evidence

ORD record: ord-14fc3f0890ad4fb7a6f7bfd3a3f0dfc8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912186B2

Reaction notes

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