Hydrochloric Acid → HCID 14135842, compound

HRID 357685Notes

Reaction equation

HRID 357685 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-5α sterol 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-def2f56bbd5b495cbe739e8365ed6097
Source dataset
uspto-grants-1998_11
Patent number
US05840936

Reaction notes

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