Tetrahydrofuran → {2-(3-Hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

HRID 2079108Notes

Reaction equation

HRID 2079108 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.[CH3:24][O:25][C:26](=[O:64])[N:27]=[C:28]([S:62][CH3:63])[C:29]([C:43]1[CH:48]=[C:47]([O:49][Si](C(C)C)(C(C)C)C(C)C)[CH:46]=[C:45]([O:60][CH3:61])[CH:44]=1)=[N:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:41]=[C:40]([CH3:42])[O:39][N:38]=2)=[CH:33][CH:32]=1.[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:24][O:25][C:26](=[O:64])[N:27]=[C:28]([S:62][CH3:63])[C:29]([C:43]1[CH:44]=[C:45]([O:60][CH3:61])[CH:46]=[C:47]([OH:49])[CH:48]=1)=[N:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:41]=[C:40]([CH3:42])[O:39][N:38]=2)=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 72312779{2-(3-Methoxy-5-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Product 1

HCID 72312820{2-(3-Hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterYield 79.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

After adding 3.3 ml of TBAF (1.0 M, THF solution) to a 15 ml THF solution containing 1.8 g of {2-(3-methoxy-5-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester, the mixture was stirred at 0° C. for 1 hour and 30 minutes. Saturated aqueous ammonium chloride was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.06 g) as a yellow solid.

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-13dfd629435a4d2bba1c6787cb3a67c3
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

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