Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21024032, compound

HRID 1795693Notes

Reaction equation

HRID 1795693 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:26][CH:27]1[C:28]([O:70]C(OCC)C)([CH3:69])[CH2:29][CH2:30][CH:31]([O:63]C(OCC)C)[CH2:32][C:33]([O:35][CH:36](/[C:41](/[CH3:62])=[CH:42]/[CH:43]=[CH:44]/[CH:45]([CH3:61])[CH2:46][CH:47]2[O:60][CH:48]2[CH:49]([CH3:59])[CH:50]([O:53]C(OCC)C)[CH2:51][CH3:52])[CH:37]([CH3:40])[CH:38]=[CH:39]1)=[O:34])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[C:18]([O:26][CH:27]1[C:28]([OH:70])([CH3:69])[CH2:29][CH2:30][CH:31]([OH:63])[CH2:32][C:33]([O:35][CH:36](/[C:41](/[CH3:62])=[CH:42]/[CH:43]=[CH:44]/[CH:45]([CH3:61])[CH2:46][CH:47]2[O:60][CH:48]2[CH:49]([CH3:59])[CH:50]([OH:53])[CH2:51][CH3:52])[CH:37]([CH3:40])[CH:38]=[CH:39]1)=[O:34])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21024031HCID 21024031, compound

Product 1

HCID 21024032HCID 21024032, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium p-toluenesulfonate (2 mg, 7.5 μmol) was added to a solution of (8E,12E,14E)-7-benzoyloxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (6.1 mg, 7.48 μmol) in methanol (1 mL), followed by stirring at room temperature for one hour. The reaction solution was evaporated, ethyl acetate, water and a saturated sodium bicarbonate aqueous solution were added to the resulting residue, and the mixture was extracted with ethyl acetate. 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 acetatehexane=2:1) to obtain the title compound (3.3 mg, 74%) as a colorless oil.

Workup

  1. customThe reaction solution was evaporated
  2. additionethyl acetate, water and a saturated sodium bicarbonate aqueous solution were added to the resulting residue
  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 acetatehexane=2:1)

Sources & evidence

ORD record
ord-e0452191cbcf44bda2e94d1c23a5b64f
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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