반응 #1869171

반응 방정식

2-Methoxyestrone

2-methoxyestrone

HCl

Hydrazine hydrate

KOH

Compound 4

2-methoxyestrone

→

Compound 7

수율 72.0%

2-Methoxyestra-1,3,5(10)-triene-3-ol

수율 72.0%

용매

ethylene glycol

n-butanol

반응 조건

후처리

1. 1
   온도The reaction was cooled to 70° C.
2. 2
   온도the reaction was heated at 200° C. for 1 h
3. 3
   온도The mixture was cooled to room temperature
4. 4
   workup.ADDITIONwas added
5. 5
   여과The resulting solid was filtered off
6. 6
   workup.DISSOLUTIONThe solid was dissolved in acetone
7. 7
   기타which was then evaporated

실험 절차

2-Methoxyestrone (Scheme 1, Compound 4) (450 mg, 1.5 mmol) was suspended in ethylene glycol (10 mL) and n-butanol (2 mL). Hydrazine hydrate (0.145 mL, 3 mmol) was added and the mixture was heated to 130° C. for 1 h. The reaction was cooled to 70° C., KOH (253 mg, 4.5 mmol) was added, then the reaction was heated at 200° C. for 1 h. The mixture was cooled to room temperature, poured into ice and HCl (6N, 6 mL) was added. The resulting solid was filtered off. The solid was dissolved in acetone, which was then evaporated to give a product (Scheme 1, Compound 7) (310 mg, 72% yield). 1H NMR (300 MHz, CDCl3) δ 6.93 (1H, s, aromatic), 6.75 (1H, s, aromatic), 5.35 (1H, s, phenol), 3.95 (3H, s, methoxy), 2.95 (2H, dd, J=5.0, 3.0 Hz), 2.25 (2H, m,), 1.95 (2H, m), 1.95-1.05 (11H, m), 0.8 (3H, s)

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