Reaktion #80531

Reaktionsgleichung

9a

(S)-2,2-Dimethyl-3-(1-oxoheptyl]-4-oxazolidinecarboxaldehyde

EtMgBr

→

10a

(4S)-α-Ethyl-2,2-dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cold bath is removed
2. 2
   workup.ADDITIONa crystal of iodine is added to the mixture
3. 3
   workup.ADDITIONThe resulting mixture is diluted with EtOAc
4. 4
   Waschenwashed with saturated aqueous NH4Cl solution
5. 5
   Sonstigethe combined organic solution dried
6. 6
   Sonstigeevaporated

Vorschrift

A solution of 9a (108 mg, 0.44 mmol) in ether (1 mL) is added dropwise to a cold (5°) solution of EtMgBr (3M in ether, 0.36 mL). The cold bath is removed, a crystal of iodine is added to the mixture and stirring is continued for 1.5 h at room temperature. The resulting mixture is diluted with EtOAc and washed with saturated aqueous NH4Cl solution. The aqueous phase is reextracted and the combined organic solution dried and evaporated to yield crude 10a: NMR δ0.88 (m, 1.05 (m, 1.30 (m, 1.45 (m, 2H), 1.57 (s, 3H), 1.50-1.75 (m, 5H), 2.10-2.60 (m, 2H), 3.50-4.50 (m, 4H); MS (EI) m/z 271 (M).

Quelle