反応 #1049539

反応方程式

(8-cyclopentyl-octyl)-triphenylphosphonium bromide

hexane

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

→

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

溶媒

tert.-butyl methyl ether

tetrahydrofuran

反応条件

後処理

1. 1
   その他prepared
2. 2
   温度by heating
3. 3
   その他3.4 g of (8-bromooctyl)-cyclopentane and 3.9 g of triphenylphosphine in 15 ml of toluene overnight and precipitation of the product
4. 4
   その他from the cooled reaction mixture
5. 5
   workup.STIRRINGThe reaction mixture is stirred at 0° C. for a further 2 hours
6. 6
   その他triturated with 10 ml of saturated sodium hydrogen carbonate solution
7. 7
   その他The phases are separated
8. 8
   洗浄the organic phase is washed with saturated sodium chloride solution
9. 9
   乾燥dried over sodium sulphate
10. 10
    ろ過filtered
11. 11
    濃縮concentrated
12. 12
    その他The residue is partitioned between methanol/water (vol.) 4:1 and hexane
13. 13
    その他the methanol phase is separated
14. 14
    洗浄The hexane phase is washed with methanol/water 4:1
15. 15
    濃縮the filtrate is concentrated

実験手順

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).

出典