Imidazole → HCID 17756279, compound

HRID 1723983Notes

Reaction equation

HRID 1723983 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][CH:5]=1.N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])[CH3:23].CCCCCC>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:25]([C:22]([CH3:24])([CH3:23])[CH3:21])([CH3:27])[CH3:26])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8058HexaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 14603109Methyl 4-(4-hydroxybutyl)benzoate

Product 1

HCID 17756279HCID 17756279, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-hydroxy-butyl)-benzoic acid methyl ester (300 mg, 1.44 mmol) in DMF (4 mL) was added imidazole (147 mg, 2.16 mmol) followed by TBDMS-Cl (324 mg, 2.16 mmol). The reaction stirred at room temperature for 2 hours, monitoring by TLC (3:1 Hexane:ethyl acetate). After consumption of the starting material, the reaction was diluted with ethyl acetate and washed with water (3×) and saturated sodium bicarbonate (1×). The organic layer was dried over sodium sulfate, filtered, and concentrated down to obtain a yellow oil (360 mg, 77% yield). This crude oil was taken on to the next step without further purification.

Workup

  1. customAfter consumption of the starting material
  2. additionthe reaction was diluted with ethyl acetate
  3. washwashed with water (3×) and saturated sodium bicarbonate (1×)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated down

Sources & evidence

ORD record
ord-d5231b642ddd43fa9ce8c9f40119842b
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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