Imidazole → HCID 23455017, compound

HRID 1680922Notes

Reaction equation

HRID 1680922 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11](O)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>CC(C)=O>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 9794177HCID 9794177, compound

Product 1

HCID 23455017HCID 23455017, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A flask is fitted with a stirring bar and charged with 5.0 grams (0.0255 mole) of 2-acetoxy-5-hydroxybenzoic acid [M. Bergmann and P. Dangschat, Berichte, 52, 371 (1919)]. After the flask is flushed with argon and cooled in an ice bath, a solution of t-butyldimethylsilylchloride (9.23 gr., 0.06122 mole) and imidazole (8.5 gr., 0.125 mole) dissolved in 20 ml of anhydrous dimethylformaldehyde (DMF) is added dropwise over a 30 minute period. The reaction mixture is stirred at room temperature overnight. The DMF is removed in vacuo. The residue is taken up in ether (75 ml) transferred to a separatory funnel and extracted with 1 N HCl (3×25 ml), 5% NaOH (3×25 ml), water (2×10 ml) and brine (20 ml). The ether extract is dried over sodium sulfate, filtered and the solvents removed in vacuo to yield 2-acetoxy-5-t-butyldimethylsilylbenzoic acid.

Workup

  1. customA flask is fitted with a stirring bar
  2. customAfter the flask is flushed with argon
  3. temperaturecooled in an ice bath
  4. additionis added dropwise over a 30 minute period
  5. customThe DMF is removed in vacuo
  6. customtransferred to a separatory funnel
  7. extractionextracted with 1 N HCl (3×25 ml), 5% NaOH (3×25 ml), water (2×10 ml) and brine (20 ml)
  8. extractionThe ether extract
  9. dry with materialis dried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-70b0428147e545f99d795d845a07a356
Source dataset
uspto-grants-1981_06
Patent number
US04276430

Reaction notes

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