Hydrochloric Acid → HCID 14135842, compound

HRID 963235Notes

Reaction equation

HRID 963235 reaction equation
CO.[O:3]=[C:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:6]([C:7](=[O:31])[CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:5]1.Cl>O1CCCC1>[O:3]=[C:4]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:6]([C:7](=[O:31])[CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14135841HCID 14135841, compound

Product 1

HCID 14135842HCID 14135842, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 3,6-dioxo-5αsterol was prepared by acid-catalyzed isomerization of the 5β sterol. To methanol (250 ml) was added the 3,6-dioxo-5β sterol 1017 (9.6 g, 24 mmol) and tetrahydrofuran (25 ml) to dissolve the sterol completely. Concentrated hydrochloric acid (12.5 ml) was added, and the reaction was allowed to proceed overnight. The solvent was then removed under vacuum to yield 9.6 g (100% yield) of methyl 3,6-dioxo-5α-cholan-24-oate 1018 (see Organic Preparations and Procedures Int. 19(2-3), 1987, 197-208; authors used base-catalyzed isomerization using sodium methoxide rather than HCl).

Workup

  1. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-be2356570cd34f58b27e2fca89a27b6b
Source dataset
uspto-grants-1998_06
Patent number
US05763430

Reaction notes

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