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

HRID 1472955Notes

Reaction equation

HRID 1472955 reaction equation
[C:1]1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:21][C@@H:22]1[C@H:28]2[C@H:29]3[C@H:38]([CH2:39][CH2:40][C@:25]2([CH2:26][CH3:27])[C:24](=[O:42])[CH2:23]1)[C@@H:37]1[C:32](=[CH:33][C:34](=[O:41])[CH2:35][CH2:36]1)[CH2:31][CH2:30]3)(=[O:20])[CH3:19]>COC(OC)(C)C>[C:18]([O:21][C@@H:22]1[C@H:28]2[C@H:29]3[C@H:38]([CH2:39][CH2:40][C@:25]2([CH2:26][CH3:27])[C:24](=[O:42])[CH2:23]1)[C@@H:37]1[C:32]([CH:33]=[C:34]([O:41][CH3:1])[CH2:35][CH2:36]1)=[CH:31][CH2:30]3)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67361589HCID 67361589, compound

Product 1

HCID 67362263HCID 67362263, compoundYield 498.3%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

Pyridinium p-Toluenesulfonate (260 mg, 1.03 mmol) was added to a suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (2 g, 5.8 mmol) in 2,2-dimethoxypropane (20 ml). The mixture was stirred under reflux for 7 h and at room temperature overnight. It was then cooled to −10° C. for 1 h. The precipitate was filtered, washed with cooled MeOH and dried under vacuum to afford 15α-acetoxy-3-methoxy-18-methyl-estra-3,5-dien-17-one (1.84 g, yield: 88%).

Workup

  1. temperatureIt was then cooled to −10° C. for 1 h
  2. filtrationThe precipitate was filtered
  3. washwashed with cooled MeOH
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5b3c7ecdd6b34e39a35327d40c3fa461
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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