Water → HCID 14986696, compound

Participants

Reaction Steps

To a solution of 0.363 g (1.5 mmol) of ethyl m-(3-pyridyl)-phenylacetate in 5.4 ml dry dimethylformamide at 5° is added 1.56 ml of a 1M solution of sodium hexamethyldisilazide in tetrahydrofuran. The organic layer is evaporated to dryness and resulting orange colored solution is stirred for 10 min and 0.54 ml (4.7 mmol) 1-bromo-4-chlorobutane is added rapidly. The reaction mixture is stirred at 5° for 2 h and then poured into water and extracted thrice with ether. The organic layer is evaporated to dryness and the resulting oil is purified by flash chromatography using 1:1 ether/hexane to obtain ethyl 6-chloro-2-[m-(3-pyridyl)-phenyl]-hexanoate; IR (CH2Cl2): 1728, 1278, 1184, 1165, 1023 cm-1.

Provenance & Evidence