Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68940746, compound

HRID 388727Notes

Reaction equation

HRID 388727 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([C@H:11]([CH3:19])[CH2:12][CH2:13][C@H:14]([CH3:18])[CH:15]([CH3:17])[CH3:16])[CH2:9][CH2:8][C@H:7]1[C@@H:6]([OH:20])[CH2:5][CH2:4][CH2:3]2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C@@:2]12[C@@H:10]([C@H:11]([CH3:19])[CH2:12][CH2:13][C@H:14]([CH3:18])[CH:15]([CH3:16])[CH3:17])[CH2:9][CH2:8][C@H:7]1[C:6](=[O:20])[CH2:5][CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 2724130Cornforth reagentHCID 57326244HCID 57326244, compound

Product 1

HCID 68940746HCID 68940746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound of Example 7B (66 mg, 0.25 mmol) was dissolved in 5 mL of dichloromethane and cooled to 0° C.; 370 mg of pyridinium dichromate and 2 mg of pyridinium p-toluenesulfonate were added, and the resultant mixture was shaken at ambient temperature for 4 hours. The reaction was filtered first through a pad of diatomaceous earth, then through a pad of silica gel, with ethyl acetate washes. The combined filtrate was concentrated and purified by chromatography on an Analogix Intelliflash 280™, eluting with 10% ethyl acetate in hexanes to provide the titled compound, 56 mg.

Workup

  1. filtrationThe reaction was filtered first through a pad of diatomaceous earth
  2. concentrationThe combined filtrate was concentrated
  3. custompurified by chromatography on an Analogix Intelliflash 280™
  4. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b77700b8662a4c9a95335b827c6f9141
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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