Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 67362263, compound

HRID 1472969Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH2:9][CH3:10])[C:7](=[O:25])[CH2:6]1)[C@@H:20]1[C:15](=[CH:16][C:17](=[O:24])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:3])[CH3:2].[C:26]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>COC(OC)(C)C>[C:1]([O:4][C@@H:5]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH2:9][CH3:10])[C:7](=[O:25])[CH2:6]1)[C@@H:20]1[C:15]([CH:16]=[C:17]([O:24][CH3:26])[CH2:18][CH2:19]1)=[CH:14][CH2:13]3)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

A suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (48 g, 139 mmol) and pyridinium p-Toluenesulfonate (4.8 g, 19.1 mmol) in 2,2-dimethoxypropane (400 ml) was refluxed for 6 h. The mixture was then cooled to −10° C. for 2 h. The precipitate was filtered, washed with cooled methanol and dried under vacuum to afford 15α-acetoxy-3-methoxy-18-methyl-estra-3,5-dien-17-one (42.7 g, yield: 86%).

Workup

temperaturewas refluxed for 6 h
filtrationThe precipitate was filtered
washwashed with cooled methanol
customdried under vacuum

Sources & evidence

ORD record: ord-bb05dcf7331e48d9bcebf28bd68a215c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012667B2

Reaction notes

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