Reaktion #11832

Reaktionsgleichung

ethyl acetate

N-(2,6-Diisopropylphenyl)-N′-(2-hydroxy-5-methylphenyl)-oxalamide

1-adamantol

H2SO4

→

solid

Ausbeute 48.4%

N-(2,6-diisopropylphenyl)-N′-(2-hydroxy-3-(adamant-1-yl)-5-methylphenyl)-oxalamide

Ausbeute 48.4%

Lösungsmittel

—

hexanes

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeaccording to the synthesis method
2. 2
   Sonstigeforming a suspension
3. 3
   workup.ADDITIONAfter addition of the acid
4. 4
   SonstigeAt this point, the solvent was removed under reduced pressure
5. 5
   workup.DISSOLUTIONthe resulting solids were redissolved in ethyl acetate (100 ml)
6. 6
   WaschenThe resulting solution was then washed with saturated NaHCO3 (3×50 ml, gas is evolved), and brine
7. 7
   Trocknendried over MgSO4
8. 8
   SonstigeThe solvent was removed under reduced pressure
9. 9
   Sonstigethe resulting solid was purified via column chromatography

Vorschrift

N-(2,6-Diisopropylphenyl)-N′-(2-hydroxy-5-methylphenyl)-oxalamide (5.59 g, 15.5 mmol, 1.0 eq), prepared according to the synthesis method described in Example 8, and 1-adamantol (2.83 g, 18.6 mmol, 1.2 eq) were dissolved in CH2Cl2 (150 ml), forming a suspension. To this suspension was then added concentrated H2SO4 (1 ml). After addition of the acid, the solids eventually went into solution. After stirring at room temperature for 24 hours, the TLC (9:1 hexanes:ethyl acetate, visualized by UV) showed that most of the starting material had gone to product. At this point, the solvent was removed under reduced pressure, and the resulting solids were redissolved in ethyl acetate (100 ml). The resulting solution was then washed with saturated NaHCO3 (3×50 ml, gas is evolved), and brine, then dried over MgSO4. The solvent was removed under reduced pressure, and the resulting solid was purified via column chromatography to give a product, light yellow solid (3.68 g, 7.5 mmol, 48%). 1H NMR (300 MHz, CDCl3) δ 9.51 (s, 1H), 8.77 (s, 1H), 7.84 (s, 1H), 7.37 (t, J=7.2 Hz 1H), 7.23 (d, J=7.5 Hz, 2H), 7.00 (d, J=2.1 Hz, 1H), 6.94 (d, J=1.8 Hz, 1H), 3.01 (septet, J=6.9, 2H), 2.29 (s, 3H), 2.18 (bs, 6H), 2.10 (bs, 3H), 1.80 (bs, 6H), 1.22 (d, J=6.9, 12H); 13C NMR (75 MHz, CDCl3) δ 158.3, 158.2, 146.2, 145.8, 140.6, 129.9, 129.2, 129.2, 126.8, 124.7, 123.8, 120.9, 40.7, 37.3, 37.1, 29.1, 29.0, 23.6, 20.8. Anal. Calcd for C31H40N2O3: C, 76.19; H, 8.25; N, 5.73. Found: C, 75.89; H, 8.42; N, 5.37.

Quelle