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28th January 2014 @ 22:28
Reaction proceeded as expected. Product was obtained in 87% yield.

START: 28/01/14
FINISH: 31/01/14

Scheme
scheme_KAB119-1.png

Hazard and Risk Assessment
HNMR KAB119-1 300 MHz CDCl3


Procedure
28/01/14. Suspended KAB8-17 in ethanol and HCl (1 M). Heated to reflux from 1500; oil bath approx. 130 ° C. Yellowish heterogenous solution.

29/01/14. 0800, clear mixture homogenous and orange. Allowed to cool. Basified to pH 11-13 using solid KOH (about 4 g). Extracted with dichloromethane (2 × 100 mL) and ethyl acetate (100 mL). Combined organic fractions were dried with Na2SO4, concetrated under reduced pressure and dried in vacuo to give an orange solid (1.49 g, 87%)

HNMR consistent with the expected product. No purification required.

Raw HNMR KAB119-1 300 MHz CDCl3
HNMR KAB119-1 300 MHz CDCl3


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23rd January 2014 @ 03:58
START: 13/02/14
FINISH: 14/02/14

Scheme
schemeKAB8-16.png
Hazard and Risk Assessment
HIRAC KAB8-17


Procedure
Dissolved MNR10-2 (6.14 g, 13.4 mmol, 1 equiv.) in toluene (500 mL). Started heating to reflux. At about 70 °C methanesulfonic acid (1.40 mL, 21.4 mmol, 1.6 equiv.). Heated to reflux; oil bath at about ~130 °C. Allowed to cool 40 min later. TLC (75% EtOAc/hexanes) indicated complete consumption of SM (KMnO4 stain) No apparent enamide present.
Reaction allowed to cool. Worked up according to MNR10.

Crude yield: 5.4 g.

Purified using column chromatography: 50 to 70 to 100% ethyl acetate/hexanes. Product obtained as an off-white foam 4.43 g, 90%.

~400 mg was saved. The remainder of the material was taken on to the next step (i.e. KAB119-2)

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