Iodide Ion → HCID 18793505, compound

Participants

Reaction Conditions

Reaction Steps

N-(1-methylethyl)-2-propanamine lithium salt (0.0325 mol; 1 M in THF) was added dropwise and under N2 flow to intermediate 4 (0.0309 mol) in THF (70 ml), cooled to -78° C. The mixture was stirred for 30 minutes at -78° C. lodomethane iodide (0.034 mol) was added dropwise and the reaction mixture was stirred for 2 hours at RT. The mixture was quenched with a saturated aqueous NH4Cl solution, and extracted with ethylacetate. The separated organic layer was dried, filtered, and the solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2), then by HPLC over silica gel (eluent: hexane/ethylacetate 3/2). The pure fractions were collected and the solvent, yielding 4.64 g (53%) of (±)-4-(difluoromethoxy)-alpha-methyl-3-[(tetrahydro-3-furanyl)oxy]benzeneacetonitrile (intermediate 9).

Provenance & Evidence