Réaction #424781

Équation de réaction

4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Methyl 3-ethenyl-1-naphthalenecarboxylate

sodium perborate

DPPB

→

title compound

Methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe aqueous layer was separated
2. 2
   Extractionback-extracted with ether
3. 3
   LavageThe combined organic extracts were then washed further with 1 N aq. NaOH, water and brine
4. 4
   SéchageThis was then dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationthe filtrate concentrated in vacuo
7. 7
   Autreto afford a pale yellow oil
8. 8
   AutrePurification of the crude product
9. 9
   Autrethus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→1:1 (v/v) EtOAc:Hex)

Mode opératoire

Methyl 3-ethenyl-1-naphthalenecarboxylate (1 eq.) from the previous step, [Ir(COD)Cl]2 (0.025 eq.) and DPPB (0.05 eq.) were combined in THF (0.12 M). To this solution was then added 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.2 eq.) and the resulting red solution was stirred at RT for 16 h. Finally, sodium perborate (0.1 M aqueous solution, 2 eq.) was added and the now black biphasic solution was vigorously stirred at RT for another 12 h. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→1:1 (v/v) EtOAc:Hex) afforded the title compound as a pale yellow oil.

Source