تفاعل #70412

معادلة التفاعل

NaHCO3

17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyimino-androstane

pTSA H2O

→

title compound

المردود 67.0%

6-(E)-Hydroxyiminoandrost-4-ene-3,17-dione

المردود 67.0%

المذيبات

acetone

acetone

ظروف التفاعل

المعالجة

1. 1
   أخرىwas evaporated
2. 2
   استخلاصThe aqueous suspension was extracted with CH2Cl2 (3×)
3. 3
   غسيلThe combined organic extracts were washed with H2O
4. 4
   تجفيفdried over Na2SO4
5. 5
   أخرىevaporated to dryness
6. 6
   أخرىThe residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 80/10/10)

الإجراء التجريبي

A solution of 3,3:17,17-bis(ethylendioxy)-5α-hydroxy-6-(E)-hydroxyimino-androstane (Prepn. 27) (1.05 g) and pTSA H2O (4.00 g) in acetone (100 mL) was stirred at room temperature for 5 h. The solution was neutralized by addition of 5% aqueous NaHCO3 and acetone was evaporated. The aqueous suspension was extracted with CH2Cl2 (3×). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 80/10/10) to give the title compound II-bw in 67% yield. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 11.60 (1H, s), 5.90 (1H, s), 3.36 (1H, d), 2.60-1.15 (16H, m), 1.08 (3H, s), 0.82 (3H, s)

المصدر