Imidazole → HCID 18352488, compound

HRID 369817Notes

Reaction equation

HRID 369817 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[Si:22]([O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18352485HCID 18352485, compound

Product 1

HCID 18352488HCID 18352488, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet was charged with 1.79 g of methyl 4-hydroxy-3-cyclopentylbenzoate, 1.22 g of imidazole (Aldrich), 30 mL of anhydrous DMF, and 1.47 g of tert-butyldimethylsilyl chloride (Aldrich). The solution was stirred at RT under nitrogen for 24 h and then concentrated in vacuo to give a thick oil. This material was subjected to flash chromatography on silica gel (95:5 hexane:EtOAc) to afford 2.43 g (89%) of methyl 4-((tert-butyldimethylsilyl)oxy)-3-cyclopentylbenzoate as a clear liquid.

Workup

  1. customA 100 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet
  2. concentrationconcentrated in vacuo
  3. customto give a thick oil

Sources & evidence

ORD record
ord-7faa25fe20df478ea1d0f7093961167a
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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