Methoxymethyl-triphenylphosphonium chloride → HCID 72237998, compound

Temperature

-78 °C

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).

1. temperatureThe reaction was cooled to −78° C.
2. additionwas added slowly
3. stirringstirred at −78° C.
4. temperatureslowly warmed to ambient temperature
5. stirringAfter stirring for 2 hours the reaction
6. customwas partitioned between EtOAc and water
7. dry with materialThe organic layer was dried with sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified on a silica gel column (15 to 25% EtOAc/hexanes)

ORD record

ord-196f1f39fea34a2caedd4ad572b67c5f

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933077B2