Reaktion #48289

Reaktionsgleichung

2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde

TESOH

(R)-2-methylpropane-2-sulfinamide

→

title compound

(R,E)-N-(2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)ethylidene)-2-methylpropane-2-sulfinamide

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir for 40 h
2. 2
   SonstigeThe copper salts were removed by celite filtration
3. 3
   EinengenThe filtrate was concentrated
4. 4
   Sonstigeto give a yellow oil that
5. 5
   Sonstigewas purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)

Vorschrift

To a 1.0 L round bottom flask containing 2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde (5.00 g, 23.3 mmol) (crude 10.5 g with TESOH, 1H NMR showed about 50/50 sm to impurity) was added DCM (200 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, (R)-2-methylpropane-2-sulfinamide (2.83 g, 23.3 mmol) and cupric sulfate anhydrous (2.58 ml, 58.3 mmol) were added and the reaction was allowed to stir for 40 h. The copper salts were removed by celite filtration. The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)to afford the title compound as a colorless oil.

Quelle