Methoxymethyl-triphenylphosphonium chloride → HCID 69411264, compound

Temperature

-78 °C

To a solution of (methoxymethyl)triphenylphosphonium chloride (533 mg, 1.55 mmol) in THF (10 ml) at 0° C. was added lithium hexamethyldisilazide (1.55 ml, 1M solution, 1.55 mmol). The reaction mixture was stirred for 0.5 h and cooled to −78° C. A solution of 2-(4-chloro-phenyl)-1-(2-chloro-phenyl)-5-formyl-1H-imidazole-4-carboxylic acid ethyl ester I-5e (408 mg, 1.05 mmol) in THF (5 ml) was slowly added via cannula. The reaction mixture was stirred at −78° C. for 5 min, then was allowed to warm to room temperature and stir for 3 hours. The reaction mixture was quenched with H2O and diluted with EtOAc. The organic solution was separated and the aqueous layer was extracted once with EtOAc. The combined EtOAc extracts were washed with sat'd aq. NaCl, dried, and concentrated in vacuo. The crude residue was purified on 4 mm chromatotron plates using 1:1 EtOAc/hexanes to give the product (I-5g) as two isomeric compounds (148 mg, 34% and 157 mg, 36%): +APCI MS (M+1) 417.2

1. stirringThe reaction mixture was stirred at −78° C. for 5 min
2. temperatureto warm to room temperature
3. stirringstir for 3 hours
4. customThe reaction mixture was quenched with H2O
5. additiondiluted with EtOAc
6. customThe organic solution was separated
7. extractionthe aqueous layer was extracted once with EtOAc
8. washThe combined EtOAc extracts were washed with sat'd aq. NaCl
9. customdried
10. concentrationconcentrated in vacuo
11. customThe crude residue was purified on 4 mm chromatotron plates
12. customto give the product (I-5g) as two isomeric compounds (148 mg, 34% and 157 mg, 36%)

ORD record

ord-37aff48aaad34137b08505d5a9301905

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07145012B2