반응 #1889313

반응 방정식

tetrahydrofuran

Triisopropyl borate

7-Benzyloxy-3-bromo-1,2-dihydro-naphthalene

toluene

tert-Butyllithium

pentane

→

6-(benzyloxy)-3,4-dihydronaphthalen-2-ylboronic acid

반응 조건

후처리

1. 1
   기타dried on the high vacuum for 30 min
2. 2
   온도cooled with a dry ice -isopropanol bath under an atmosphere of nitrogen
3. 3
   workup.STIRRINGthe mixture was stirred for 1 hour
4. 4
   온도with cooling
5. 5
   기타then brought to r.t
6. 6
   기타The reaction was quenched with ice-water
7. 7
   기타The organic layer was separated
8. 8
   추출the aqueous layer was extracted with EtOAc (3×50 mL)
9. 9
   세척The combined organic layers were washed with water, brine
10. 10
    건조dried over anhydrous Na2SO4
11. 11
    여과filtered
12. 12
    농축concentrated
13. 13
    기타dried on the high vacuum

실험 절차

7-Benzyloxy-3-bromo-1,2-dihydro-naphthalene (21.75 g, 0.06900 mol) was azeotroped with toluene (100 mL, 0.9 mol) and dried on the high vacuum for 30 min. This was dissolved in tetrahydrofuran (200 mL, 2 mol), cooled with a dry ice -isopropanol bath under an atmosphere of nitrogen. 1.70 M tert-Butyllithium in pentane (89.3 mL, 0.152 mol) was added slowly, stirred for 10 min. Triisopropyl borate (79.1 mL, 0.345 mol) was added and the mixture was stirred for 1 hour with cooling then brought to r.t. The reaction was quenched with ice-water. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered, concentrated and dried on the high vacuum to give a crude intermediate, 6-(benzyloxy)-3,4-dihydronaphthalen-2-ylboronic acid.

출처