반응 #1049539

반응 방정식

(8-cyclopentyl-octyl)-triphenylphosphonium bromide

hexane

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

→

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

용매

tert.-butyl methyl ether

tetrahydrofuran

반응 조건

후처리

1. 1
   기타prepared
2. 2
   온도by heating
3. 3
   기타3.4 g of (8-bromooctyl)-cyclopentane and 3.9 g of triphenylphosphine in 15 ml of toluene overnight and precipitation of the product
4. 4
   기타from the cooled reaction mixture
5. 5
   workup.STIRRINGThe reaction mixture is stirred at 0° C. for a further 2 hours
6. 6
   기타triturated with 10 ml of saturated sodium hydrogen carbonate solution
7. 7
   기타The phases are separated
8. 8
   세척the organic phase is washed with saturated sodium chloride solution
9. 9
   건조dried over sodium sulphate
10. 10
    여과filtered
11. 11
    농축concentrated
12. 12
    기타The residue is partitioned between methanol/water (vol.) 4:1 and hexane
13. 13
    기타the methanol phase is separated
14. 14
    세척The hexane phase is washed with methanol/water 4:1
15. 15
    농축the filtrate is concentrated

실험 절차

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).

출처