Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86604549, compound
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
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
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
- 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-eba8b82f069946e3841400da770ed014
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026352B1
Reaction notes
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