Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 58619154, compound

HRID 1795695Notes

Reaction equation

HRID 1795695 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(OC([O:23][C:24]1([CH3:61])[CH:36]([OH:37])[CH:35]=[CH:34][CH:33]([CH3:38])[CH:32](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51]C(OCC)C)[CH2:49][CH3:50])[O:31][C:29](=[O:30])[CH:28]=[CH:27][CH2:26][CH2:25]1)C)C>CO>[OH:23][C:24]1([CH3:61])[CH:36]([OH:37])[CH:35]=[CH:34][CH:33]([CH3:38])[CH:32](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([OH:51])[CH2:49][CH3:50])[O:31][C:29](=[O:30])[CH:28]=[CH:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86604546HCID 86604546, compound

Product 1

HCID 58619154HCID 58619154, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium p-toluenesulfonate (2 mg, 7.7 μmol) was added to a solution of (2Z,8E,12E,14E)-6,21-di(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-2,8,12,14-tetraen-11-olide (6.3 mg, 10.1 μmol) in methanol (1.5 mL), followed by stirring at room temperature for one hour. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate, water and a saturated sodium bicarbonate aqueous solution. The mixture was extracted with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane=4:3) to obtain the title compound (3.3 mg, 68%) as a colorless oil.

Workup

  1. customThe reaction solution was evaporated
  2. additionto the resulting residue were added ethyl acetate, water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane=4:3)

Sources & evidence

ORD record
ord-aebfc05e2e83408aacbd17777875445c
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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