Reaktion #1884611

Reaktionsgleichung

43

(4S, 5S)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(dimethylphenylsilyl)methyl]-1-cyclopentene-1-carboxylic acid methyl ester

diisobutylaluminum hydride

→

crude title compound

Ausbeute 100.0%

(4S, 5S)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-5-[(dimethylphenylsilyl)methyl]-1-cyclopentene-1-methanol

Ausbeute 100.0%

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe temperature below −60° C
2. 2
   Sonstigethe reaction
3. 3
   SonstigeThe reaction mixture was quenched by addition of sodium hydroxide (2 N, 200 mL)
4. 4
   SonstigeThe organic layer was separated
5. 5
   Waschenwashed with water, brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   EinengenThe organic layer was concentrated in vacuo to dryness

Vorschrift

To a solution of 43 (15 g, 37.13 mmol) in hexanes (100 mL) was added diisobutylaluminum hydride (113 mL, 113.4 mmol, 1 N in hexanes) at −78° C. slowly over a period of 30 minutes keeping the temperature below −60° C. The resulting mixture was stirred for 2 hours at the same temperature to complete the reaction. The reaction mixture was quenched by addition of sodium hydroxide (2 N, 200 mL). The organic layer was separated and washed with water, brine, and dried over magnesium sulfate. The organic layer was concentrated in vacuo to dryness to give the crude title compound (13 g, 100% yield).

Quelle