반응 #81529

반응 방정식

methyl trifluoromethylsulfonate

diethyl 3-hydroxyglutarate

2,6-di-tert-butylpyridine

HCl

→

expected product

3-Methoxypentane-1,5-diol

용매

THF

DCM

반응 조건

후처리

1. 1
   온도the mixture is refluxed for 5 hours
2. 2
   온도After cooling
3. 3
   기타the organic phase is decanted
4. 4
   건조dried over magnesium sulfate
5. 5
   기타the solvent is evaporated off under vacuum
6. 6
   기타The solid obtained
7. 7
   여과the mixture is filtered
8. 8
   workup.ADDITION160 ml of a 1M solution of lithium aluminum hydride in THF are then added slowly
9. 9
   기타to rise to RT
10. 10
    온도The reaction mixture is cooled to 0° C.
11. 11
    workup.ADDITION5.5 ml of water, 18 ml of a 15% solution of NaOH and 5.5 ml of water are added successively
12. 12
    여과The mineral salts are filtered off
13. 13
    기타the filtrate is evaporated under vacuum

실험 절차

25 ml of methyl trifluoromethylsulfonate are added to a solution of 30 g of diethyl 3-hydroxyglutarate and 33 ml of 2,6-di-tert-butylpyridine in 500 ml of DCM and the mixture is refluxed for 5 hours. After cooling, 500 ml of a 0.5N solution of HCl are added, the organic phase is decanted and dried over magnesium sulfate and the solvent is evaporated off under vacuum. The solid obtained is taken up with 200 ml of anhydrous THF, the mixture is filtered and the filtrate is then cooled to -5° C. 160 ml of a 1M solution of lithium aluminum hydride in THF are then added slowly and the mixture is stirred for 16 hours, the temperature being allowed to rise to RT. The reaction mixture is cooled to 0° C. and 5.5 ml of water, 18 ml of a 15% solution of NaOH and 5.5 ml of water are added successively. The mineral salts are filtered off and the filtrate is evaporated under vacuum to give the expected product after distillation under reduced pressure. B.p.=104° C. under 1.5 Pa.

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