Methoxymethyl-triphenylphosphonium chloride → 1-[2-Bis(4-fluorophenyl)methoxyethyl]-4-methoxymethylidenepiperidine

Temperature

-10 °C

Meanwhile, 1.066 g of methoxymethyltriphenylphosphonium chloride was added to 7 ml of tetrahydrofuran, and the mixture was cooled at -10° C. The lithium diisopropylamide solution previously prepared was then added to this mixture, which was then stirred for 30 minutes at -10° C. At the end of this time, 5 ml of a tetrahydrofuran solution containing 1.01 g of 1-[2-bis(4-fluorophenyl)methoxyethyl]-4-piperidone (prepared as described in preparation 6) were dropped into the reaction mixture, at -10° C. The mixture was stirred for 30 minutes, allowed to stand overnight at room temperature, and then condensed by evaporation under reduced pressure. Water was added to the residue, which was then extracted with ethyl acetate. The oily substance obtained was purified by silica gel column chromatography. Elution with a 2:1 by volume mixture of ethyl acetate and hexane afforded 718 mg (yield 66%) of a yellow oily substance.

1. additionwas then added to this mixture, which
2. additionwere dropped into the reaction mixture, at -10° C
3. stirringThe mixture was stirred for 30 minutes
4. waitto stand overnight at room temperature
5. customcondensed
6. customby evaporation under reduced pressure
7. additionWater was added to the residue, which
8. extractionwas then extracted with ethyl acetate
9. customThe oily substance obtained
10. customwas purified by silica gel column chromatography
11. washElution with a 2:1
12. additionby volume mixture of ethyl acetate and hexane
13. customafforded 718 mg (yield 66%) of a yellow oily substance

ORD record

ord-2f9d1037f93f4dd58e31e016cf80bf43

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05294623