Reaktion #64858

Reaktionsgleichung

cis-4-tetrahydropyranyloxy-2-butene-1-ol

triphenyl phosphine

phthalimide

diethylazodicarboxylate

→

title compound

Ausbeute 64.0%

CIS-1-PHTHALIMIDO-4-TETRAHYDROPYRANYLOXY-2-BUTENE

Ausbeute 64.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONWhen the addition
2. 2
   Sonstige(5 min)
3. 3
   EinengenThen the mixture was concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with ethyl acetate (200 ml)
5. 5
   Waschenwashed with brine (150 ml)
6. 6
   ExtraktionAfter usual work-up (the aqueous phase was extracted three times with 100 ml portions of ethyl acetate), the organic phase
7. 7
   Trocknenwas dried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo) the product
10. 10
    Sonstigewas purified by flash chromatography on silica gel (ethyl acetate:hexane; 2:8)

Vorschrift

Under a nitrogen atmosphere diethylazodicarboxylate (1.6 ml, 10 mmol) was added to a cooled (0° C.) solution of cis-4-tetrahydropyranyloxy-2-butene-1-ol (1.7 g, 10 mmol), triphenyl phosphine (2.2 g, 10 mmol) and phthalimide (1.47 g, 10 mmol) in anhydrous tetrahydrofuran (50 ml). When the addition was completed (5 min) the reaction mixture was allowed to warm at room temperature and was stirred 12 h. Then the mixture was concentrated in vacuo, diluted with ethyl acetate (200 ml) and washed with brine (150 ml). After usual work-up (the aqueous phase was extracted three times with 100 ml portions of ethyl acetate), the organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo) the product was purified by flash chromatography on silica gel (ethyl acetate:hexane; 2:8) to give 1.9 g of the title compound (64%).

Quelle