Imidazole → 2-Chloroethyl 3-t-butyldimethylsilyloxybenzoate

HRID 2392968Notes

Reaction equation

HRID 2392968 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([O:7][CH2:8][CH2:9][Cl:10])=[O:6].[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1.O>CN(C=O)C>[Si:14]([O:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([O:7][CH2:8][CH2:9][Cl:10])=[O:6])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 151587912-Chloroethyl 3-hydroxybenzoate

Product 1

HCID 151587922-Chloroethyl 3-t-butyldimethylsilyloxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g (50 mmol) the ester from step (a), t-butyldimethylsilyl chloride (8.25 g, 55 mmol) and imidazole (4.76 g, 70 mmol) in 100 mL of DMF was stirred under argon for 1 h. The solution was poured into 100 mL of water and extracted with ether (3×50 mL). The combined ether solutions were extracted with 20 mL of water. The organic layer was dried and evaporated giving 18 g of an oil which was purified by column chromatography using 0-2% ethyl acetate in hexane yielding 14.4 g of the product as a colorless oil (91%); 1H NMR (CDCl3) δ0.218 (s,6H), 0.995 (s,9H), 3.81 (t,2H), 4.56 (t,2H), 7.05-7.65 (m,4H). ##STR13##

Workup

  1. extractionextracted with ether (3×50 mL)
  2. extractionThe combined ether solutions were extracted with 20 mL of water
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-f0c4a06d57e04e90a69c95ee986cd427
Source dataset
uspto-grants-1998_09
Patent number
US05804103

Reaction notes

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