Imidazole → Ethyl 3-(4-t-butyldimethylsilyloxyphenyl)propionate

HRID 1774375Notes

Reaction equation

HRID 1774375 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1>CN(C)C=O>[Si:15]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2736435Ethyl 4-hydroxyhydrocinnamate

Product 1

HCID 11500531Ethyl 3-(4-t-butyldimethylsilyloxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-(4-hydroxyphenyl)propionate (940 mg, 4.84 mmol) in anhydrous dimethylformamide (9.4 mL) were added t-butyldimethylsilyl chloride (1.0 g, 6.6 mmol) and imidazole (490 mg, 1.5 mmol) at room temperature, and the mixture was left standing at the same temperature for 14 h. The reaction mixture was directly concentrated, and subjected to silica gel column chromatography (hexane-ethyl acetate 25:1→20:1) to give 1.49 g (quantitative) of the title compound as a solid.

Workup

  1. waitthe mixture was left
  2. concentrationThe reaction mixture was directly concentrated

Sources & evidence

ORD record
ord-ccfa293c10b94bfdb06c22d3fec5ec91
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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