Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21024013, compound

HRID 1795679Notes

Reaction equation

HRID 1795679 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:66]C(OCC)C)([CH3:65])[CH2:24][CH2:25][CH:26]([O:58][C:59](=[O:64])[CH2:60][O:61][CH2:62][CH3:63])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:57])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:56])[CH2:41][CH:42]2[O:55][CH:43]2[CH:44]([CH3:54])[CH:45]([O:48]C(OCC)C)[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:66])([CH3:65])[CH2:24][CH2:25][CH:26]([O:58][C:59](=[O:64])[CH2:60][O:61][CH2:62][CH3:63])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:57])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:56])[CH2:41][CH:42]2[O:55][CH:43]2[CH:44]([CH3:54])[CH:45]([OH:48])[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 21024012HCID 21024012, compound

Product 1

HCID 21024013HCID 21024013, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridinium p-toluenesulfonate (9.8 mg, 0.039 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3-ethoxyacetoxy-6,21-bis(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (6.0 mg, 0.0078 mmol) in methanol (1.0 mL) at room temperature, followed by stirring at the same temperature for 15 hours. The reaction mixture was diluted with 15 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 Silicagel 60 F254, 0.2 mm, developing solution; ethyl acetate) to obtain the title compound (1.7 mg, 35%) as a colorless 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 Silicagel 60 F254, 0.2 mm, developing solution; ethyl acetate)

Sources & evidence

ORD record
ord-39b682feadd14d68beb4468f288f0ad5
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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