ChemicalBook CAS DataBase List 5B-CHOL-11-ENIC ACID-3A-OL

5B-CHOL-11-ENIC ACID-3A-OL synthesis

10synthesis methods

Product Name:5B-CHOL-11-ENIC ACID-3A-OL
CAS Number:1053-37-8
Molecular formula:C24H38O3
Molecular Weight:374.5567

434-13-9 Synthesis

434-13-9
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1053-37-8
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Yield:1053-37-8 87%

Reaction Conditions:

with potassium carbonate in tetrahydrofuran;methanol at 60 - 70;Inert atmosphere;

Steps:

7 2.2.7. Synthesis of 3α-hydroxy-5β-chol-11-en-oic acid (6)

General procedure: To a solution of 5 (18.4 g, 42.5 mmol) in a mixed solvent (150 mL)of CH3OH-THF (4:1, v/v) was added anhydrous potassium carbonate(58.7 g, 425 mmol) under N2. The reaction mixture was stirred for 24 hat 60 °C, and then poured into 2M HCl (250 mL). The mixture wasextracted with DCM (60 mL ×3). The organic layer was washed withbrine, dried over anhydrous Na2SO4 and concentrated.compound 6 was obtainedas a white solid; yield: 87%. 1H NMR (400 MHz, DMSO-d6) δ: 11.94 (s,1H), 6.05 (dd, J = 10.4, 2.8 Hz, 1H), 5.40 (d, J = 10.0 Hz, 1H), 4.43 (s,1H), 3.41-3.36 (m, 1H), 0.95 (d, J = 6.4 Hz, 3H), 0.82 (s, 3H), 0.69 (s,3H). 13C NMR (100 MHz, DMSO-d6) δ: 174.8, 138.2, 125.6, 69.7, 53.2,51.4, 44.5, 42.7, 40.6, 37.0, 35.4, 34.9, 34.6, 33.9, 30.7, 30.5, 30.3,27.9, 27.7, 25.2, 23.6, 22.6, 18.1, 16.5. HRMS (ESI) m/z: calcd forC24H38NaO3 [M+Na]+, 397.2719, found 397.2717.

References:

He, Xiao-Long;Xing, Yajing;Gu, Xiang-Zhong;Xiao, Jie-Xin;Wang, Ying-Ying;Yi, Zhengfang;Qiu, Wen-Wei [Steroids,2017,vol. 125,p. 54 - 60]