Reacción #1049539

Ecuación de reacción

(8-cyclopentyl-octyl)-triphenylphosphonium bromide

hexane

2-(4-heptyloxy-phenyl)-pyrimidine-5-carboxaldehyde

→

5-(9-cyclopentyl-non-1-enyl)-2-(4-heptyloxy-phenyl)-pyrimidine

Disolventes

tert.-butyl methyl ether

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   Temperaturaby heating
3. 3
   Otro3.4 g of (8-bromooctyl)-cyclopentane and 3.9 g of triphenylphosphine in 15 ml of toluene overnight and precipitation of the product
4. 4
   Otrofrom the cooled reaction mixture
5. 5
   workup.STIRRINGThe reaction mixture is stirred at 0° C. for a further 2 hours
6. 6
   Otrotriturated with 10 ml of saturated sodium hydrogen carbonate solution
7. 7
   OtroThe phases are separated
8. 8
   Lavadothe organic phase is washed with saturated sodium chloride solution
9. 9
   Secadodried over sodium sulphate
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated
12. 12
    OtroThe residue is partitioned between methanol/water (vol.) 4:1 and hexane
13. 13
    Otrothe methanol phase is separated
14. 14
    LavadoThe hexane phase is washed with methanol/water 4:1
15. 15
    Concentraciónthe filtrate is concentrated

Procedimiento

A suspension of 3.7 g of (8-cyclopentyl-octyl)-triphenylphosphonium bromide (prepared by heating 3.4 g of (8-bromooctyl)-cyclopentane and 3.9 g of triphenylphosphine in 15 ml of toluene overnight and precipitation of the product from the cooled reaction mixture by addition of hexane) in 20 ml of tert.-butyl methyl ether is treated with 0.8 g of potassium tert.-butylate and the yellow suspension is stirred at room temperature for 45 minutes. Then, a solution of 1.64 g of 2-(4-heptyloxy-phenyl)-pyrimidine-5-carboxaldehyde in 10 ml of tetrahydrofuran is added dropwise at 0° to 5° C. The reaction mixture is stirred at 0° C. for a further 2 hours and then triturated with 10 ml of saturated sodium hydrogen carbonate solution. The phases are separated and the organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue is partitioned between methanol/water (vol.) 4:1 and hexane and the methanol phase is separated. The hexane phase is washed with methanol/water 4:1 and the filtrate is concentrated. The crude 5-(9-cyclopentyl-non-1-enyl)-2-(4-heptyloxy-phenyl)-pyrimidine obtained is purified by chromatography on 10 g of silica gel with hexane/ethyl acetate 19:1 (v/v).

Fuente