Water → HCID 72312790, compound

HRID 1161497Notes

Reaction equation

HRID 1161497 reaction equation
[CH3:1][O:2][C:3](=[O:39])[N:4]=[C:5]([S:37][CH3:38])[C:6]([C:20]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[C:22]([O:28][Si](C(C)(C)C)(C)C)[C:21]=1[F:36])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(OCC)(=O)C.O>C1COCC1>[CH3:1][O:2][C:3](=[O:39])[N:4]=[C:5]([S:37][CH3:38])[C:6]([C:20]1[CH:25]=[C:24]([CH2:26][CH3:27])[CH:23]=[C:22]([OH:28])[C:21]=1[F:36])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 72312770HCID 72312770, compound

Product 1

HCID 72312790HCID 72312790, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.76 g of {2-[3-(t-butyldimethylsilanyloxy)-5-ethyl-2-fluorophenyl]-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 30 ml of THF there was added 1.6 ml of TBAF (1.0 M, THF solution) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 hours, and then 200 ml of ethyl acetate and 100 ml of water were added. The organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order and dried over anhydrous magnesium sulfate, the desiccating agent was filtered, 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 (0.41 g) as a white solid.

Workup

  1. washThe organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe desiccating agent was filtered
  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-fd40f8df9f514d0ea2d3c25c33b95d06
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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