19-Hydroxyprogesterone synthesis
- Product Name:19-Hydroxyprogesterone
- CAS Number:596-63-4
- Molecular formula:C21H30O3
- Molecular Weight:330.46
2205-86-9
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596-63-4
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$28.60/1mg
Yield:596-63-4 86 %
Reaction Conditions:
with acetic acid;zinc in isopropyl alcohol;Mechanism;Reflux;Inert atmosphere;
Steps:
19-Hydroxyprogesterone (1)
A mixture of compound 7 (9.8 g, 0.030 mol), Zinc (17.55 g, 0.27 mol), acetic acid(11 ml, 0.18 mol) in 350 ml i-PrOH was refluxed under Ar atmosphere for 8 h, and then the suspension was filtered, and the filter cake was washed with 100 ml i-PrOH.The combined filtrated was evaporated under vacuum, and then 300 ml DCM and100 ml water were added to the residue, and the organic layer was separated, dried over Na2SO4. The solvent was evaporated under vacuum and the target product(8.50 g) was obtained in 86.0% yield by flash column with PE:EA 2:1 as eluent, mp171 C172 C. 1H-NMR (CDCl3, 500 MHz): d 0.59 (s, 3H, 18-Me), 0.99-1.11 (m,3H), 1.16-1.23 (m, 1H), 1.29-1.48 (m, 3H), 1.54-1.76 (m, 7H), 1.81-1.89 (m, 1H),2.05 (s, 3H, 21-Me), 2.24-2.37 (m, 4H), 2.43-2.54 (m, 1H), 2.63-2.73 (m, 1H),3.81-3.86 (m, 1H, C19-H), 3.99 (d, J12.9 Hz, 1H, C19-H), 5.87 (s, 1H, C4-H). 13CNMR(CDCl3, 125 MHz): d 12.4, 20.5, 21.8, 23.3, 30.5, 31.1, 32.4, 32.5, 34.0, 35.2,38.0, 42.8, 43.0, 52.8, 55.4, 62.4, 64.8, 125.8, 166.1, 199.2, 208.4. HRESIMS: m/z353.2099 [MNa] (calcd for C21H30O3Na, 353.2093).
References:
Wang, Yan;Dong, Wei;Zhang, Qin;Li, Zhen-Peng;Wang, Yue-Xing;Li, Xiu-Fen;Huang, Long-Jiang [Journal of Asian Natural Products Research,2022]
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88204-49-3
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596-63-4
19 suppliers
$28.60/1mg
1778-02-5
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$12.00/1mg
596-63-4
19 suppliers
$28.60/1mg
145-13-1
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$30.00/20mg
596-63-4
19 suppliers
$28.60/1mg
2723-07-1
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596-63-4
19 suppliers
$28.60/1mg