Methanol → HCID 76617831, compound

HRID 2105872Notes

Reaction equation

HRID 2105872 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]2[CH:32]([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=3)[NH:31][C:30]([C:40]3[CH:45]=[CH:44][C:43]([C:46]#[C:47][Si](C)(C)C)=[CH:42][C:41]=3[O:52][CH2:53][CH3:54])=[N:29]2)=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([CH:28]2[CH:32]([C:33]3[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=3)[NH:31][C:30]([C:40]3[CH:45]=[CH:44][C:43]([C:46]#[CH:47])=[CH:42][C:41]=3[O:52][CH2:53][CH3:54])=[N:29]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 68872214HCID 68872214, compound

Product 1

HCID 76617831HCID 76617831, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride in tetrahydrofuran (3.45 mL, 3.45 mmol) was added dropwise to a solution of methanol (1.33 mL) and 4,5-bis-(4-chlorophenyl)-2-(2-ethoxy-4-trimethylsilanylethynylphenyl)-4,5-dihydro-1H-imidazole (3.50 g, 6.90 mmol) in tetrahydrofuran (70 mL) cooled in an ice bath. After stirring for 30 min, the reaction mixture was poured into saturated aqueous ammonium chloride (100 mL) and extracted with methylene chloride (300 mL, 2×100 mL). The combined organic phases were dried over magnesium sulfate and evaporated. The residue was purified by flash column chromatography (silica gel, eluting with 2% methanol in chloroform) to give 4,5-bis-(4-chlorophenyl)-2-(2-ethoxy-4-ethynylphenyl)-4,5-dihydro-1H-imidazole as a yellow foam (2.66 g, 89%). LC-MS: 435.2 [(M+H)+].

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with methylene chloride (300 mL, 2×100 mL)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash column chromatography (silica gel, eluting with 2% methanol in chloroform)

Sources & evidence

ORD record
ord-1f3bf267fc1245bbb6b9800b3f81e449
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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