Methoxymethyl-triphenylphosphonium chloride → HCID 72237998, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mL round-bottomed flask was charged with (methoxymethyl)triphenylphosphonium chloride (6.8 g, 20 mmol), THF (40 mL) and cooled to −78° C. under nitrogen. Butyllithium (8.0 ml, 20 mmol) was slowly added and stirred for 30 min at 0° C. The reaction was cooled to −78° C. and 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (2.6 g, 8.0 mmol) dissolved in THF (10 mL) was added slowly and stirred at −78° C. and slowly warmed to ambient temperature. After stirring for 2 hours the reaction was partitioned between EtOAc and water. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on a silica gel column (15 to 25% EtOAc/hexanes) to afford the title compound (2.0 g, 71% yield) as a pale yellow foam (about a 1:1 mixture of E and Z isomers). Mass spectrum (apci) m/z=354.1 (M+H).

Provenance & Evidence