Reaktion #88931

Reaktionsgleichung

diisobutyl aluminium hydride

Intermediate 61a

5-Iodo-2-triisopropylsilanyloxy-benzoic acid methyl ester

diisobutyl aluminium hydride

→

title compound

Ausbeute 39.0%

(5-Iodo-2-triisopropylsilanyloxy-phenyl)-methanol

Ausbeute 39.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to 0° C.
2. 2
   workup.STIRRINGstirred at RT for 1 h
3. 3
   TemperaturThe mixture was cooled to 0° C.
4. 4
   Sonstigequenched by dropwise addition of water
5. 5
   Sonstigeto give a gel that
6. 6
   Sonstigewas partitioned between EtOAc/ether and brine/water/aqueous potassium sodium tartrate solution
7. 7
   FiltrationThe insoluble salts were filtered off
8. 8
   Sonstigethe phases separated
9. 9
   ExtraktionThe aqueous phase was extracted with EtOAc (2×)
10. 10
    Waschenthe combined organic layers were washed with a 10% aqueous citric acid solution, saturated sodium bicarbonate solution and brine
11. 11
    Trocknendried (Na2SO4)
12. 12
    Filtrationfiltered
13. 13
    Sonstigeevaporated in vacuo
14. 14
    Sonstigepurified by FCC

Vorschrift

A solution of Intermediate 61a (2.88 g, 6.60 mmol) in DCM (50 mL) at 0° C. under N2 was treated dropwise with diisobutyl aluminium hydride (1.0M in THF, 16.6 mL, 16.6 mmol) and the mixture was stirred at RT overnight. The mixture was cooled to 0° C., then treated dropwise with another portion of diisobutyl aluminium hydride (1.0M in THF, 8.3 mL, 8.30 mmol) and stirred at RT for 1 h. The mixture was cooled to 0° C. and quenched by dropwise addition of water to give a gel that was partitioned between EtOAc/ether and brine/water/aqueous potassium sodium tartrate solution. The insoluble salts were filtered off and the phases separated. The aqueous phase was extracted with EtOAc (2×) and the combined organic layers were washed with a 10% aqueous citric acid solution, saturated sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was pre-adsorbed onto diatomaceous earth and purified by FCC, using 0-15% EtOAc in cyclohexane, to give the title compound as a colorless oil (1.04 g, 39%). LCMS (Method 3): Rt 5.29 min, m/z 405 [MH+].

Quelle