Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21024036, compound

HRID 1446639Notes

Reaction equation

HRID 1446639 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Cl:18][CH2:19][C:20]([O:22][CH:23]1[C:24]([O:66]C(OCC)C)([CH3:65])[CH2:25][CH2:26][CH:27]([O:59]C(OCC)C)[CH2:28][C:29]([O:31][CH:32](/[C:37](/[CH3:58])=[CH:38]/[CH:39]=[CH:40]/[CH:41]([CH3:57])[CH2:42][CH:43]2[O:56][CH:44]2[CH:45]([CH3:55])[CH:46]([O:49]C(OCC)C)[CH2:47][CH3:48])[CH:33]([CH3:36])[CH:34]=[CH:35]1)=[O:30])=[O:21]>CO>[Cl:18][CH2:19][C:20]([O:22][CH:23]1[C:24]([OH:66])([CH3:65])[CH2:25][CH2:26][CH:27]([OH:59])[CH2:28][C:29]([O:31][CH:32](/[C:37](/[CH3:58])=[CH:38]/[CH:39]=[CH:40]/[CH:41]([CH3:57])[CH2:42][CH:43]2[O:56][CH:44]2[CH:45]([CH3:55])[CH:46]([OH:49])[CH2:47][CH3:48])[CH:33]([CH3:36])[CH:34]=[CH:35]1)=[O:30])=[O:21]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21024035HCID 21024035, compound

Product 1

HCID 21024036HCID 21024036, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridinium p-toluenesulfonate (1 mg, 4.1 μmol) was added to a solution of (8E,12E,14E)-7-chloroacetoxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (3.2 mg, 4.06 μmol) in methanol (1 mL), followed by stirring at room temperature for one hour. The reaction solution was evaporated, and the resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane=2:1) to obtain the title compound (1.6 mg, 70%) as a colorless oil.

Workup

  1. customThe reaction solution was evaporated
  2. customthe resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane=2:1)

Sources & evidence

ORD record
ord-f0203d160f5649299e1097c7246d7d23
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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