Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86604549, compound

HRID 1446651Notes

Reaction equation

HRID 1446651 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:21][CH:22]1[C:23]([O:56]C(OCC)C)([CH3:55])[CH2:24][CH2:25][CH:26]([O:49]C(OCC)C)[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:48])=[CH:37]/[CH:38]=[CH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[CH3:19]>CO.C(OCC)(=O)C>[C:18]([O:21][CH:22]1[C:23]([OH:56])([CH3:55])[CH2:24][CH2:25][CH:26]([OH:49])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:48])=[CH:37]/[CH:38]=[CH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[CH3:19]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86604548HCID 86604548, compound

Product 1

HCID 86604549HCID 86604549, compoundYield 49.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridinium p-toluenesulfonate (13 mg, 0.051 mmol) was added to a solution of (8E,12E)-7-acetoxy-3,6-bis(1-ethoxyethoxy)-6,10,12-trimethyltricosa-8,12,14-trien-11-olide (3.2 mg, 0.0051 mmol) in methanol (1 mL) at room temperature, followed by stirring at the same temperature for 2.5 hours. The reaction mixture was diluted with 1 mL of ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crude product was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.25 mm, developing solution; hexane:ethyl acetate=1:2) to give the title compound (1.2 mg, 49%) as a pale yellow oil.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting crude product was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.25 mm, developing solution; hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-1155d09986f946fd8587263eb659f87f
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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