Reaktion #447097

Reaktionsgleichung

α-cyanobenzyl alcohol

trimethylsilylcyanide

benzaldehyde

benzaldehyde

→

(R)-(+)-α-cyanobenzyl alcohol

Ausbeute 37.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml)
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   workup.STIRRINGstirred at room temperature
4. 4
   Sonstigeto obtain a homogeneous solution
5. 5
   workup.STIRRINGstirred at room temperature for 15 hours
6. 6
   workup.ADDITIONThereafter, the reaction mixture was treated in the same manner as in Example 1
7. 7
   Sonstigewas produced in the yield of 37%

Vorschrift

To a solution of L(+)-diisopropyl tartarate (235 mg) in absolute dichloromethane (10 ml), tetaraisopropyl titanate (284 mg) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, dichloromethane (10 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (436 mg) and then benzaldehyde (424 mg) were added and stirred at room temperature for 15 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 1 and analyzed by HPLC to reveal that α-cyanobenzyl alcohol containing the R(+) isomer in the enantiomer excess percentage of 88% was produced in the yield of 37% based on the amount of the used benzaldehyde and 148% based on the amount of the used catalyst.

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