Iodoethane → HCID 18172351, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium diisopropylamide (6.5 mL, 2.0 M in heptane/THF/ethylbenzene) in THF (25.0 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (5.0 mL) was added methyl 3-(4-(benzyloxy)phenyl)propanoate 23.1 (3.00 g, 11 mmol) in THF (10 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2.5 mL) at −78° C. The resulting mixture was stirred at −78° C. for 30 minutes and then iodoethane (1.0 mL, 13 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL), and the mixture was concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with brine (2×25 mL), and dried with Na2SO4. The residue was purified by silica gel column (eluent with hexane/EtOAc; 85/15) to give the title compound 32.1. MS ESI (pos.) m/e: 299.0 (M+H)+.

Provenance & Evidence