반응 #64049

반응 방정식

water

3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one

pyridine

acetyl chloride

→

3-hydroxy-5-(3-acetamido-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one

수율 34.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGshaken
2. 2
   기타The organic layer was separated
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타the solvent was removed under reduced pressure
5. 5
   기타a rotary evaporator
6. 6
   기타The product was purified by chromatograpy over silica gel (eluent 1% methanol in dichloromethane)

실험 절차

A solution of 3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (2.6 g; 8.6 mmole) and pyridine (0.7 g; 9 mmole) in dichloromethane (100 ml) was treated with acetyl chloride (0.69 g; 9 mmole) at 20° C. with stirring. After 1.5 hours the mixture was poured into water (100 ml) and shaken. The organic layer was separated and dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure using a rotary evaporator. The product was purified by chromatograpy over silica gel (eluent 1% methanol in dichloromethane) to give 3-hydroxy-5-(3-acetamido-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (1.0 g, 34%) as a pale orange semi-crystalline solid. Proton magnetic resonance spectrum (CDCl3, δ in ppm): 1.20 (3H, t); 2.18 (3H, s); 2.20 (3H, s); 2.27 (3H, s); 2.35 (3H, s); 2.4-4.0 (7H, m) 6.6 (1H, bs); 6.88 (1H, s); 18.20 (1H, s).

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