Imidazole → 3-[(Tert-butyldimethylsilyl)oxy]phenol

HRID 1051103Notes

Reaction equation

N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C:14]1([CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[CH:16]=1)[OH:15]>CN(C)C=O>[Si:6]([O:15][C:14]1[CH:16]=[C:17]([OH:18])[CH:19]=[CH:20][CH:21]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 60 °C

Procedure

Imidazole (4.3 g, 62 mmol) and t-butyldimethylsilylchloride (5.5 g, 36 mmol) were added to a solution of resorcinol (2.8 g, 25 mmol) and dimethylformamide (100 mL) in a 250 mL round bottom flask under a nitrogen atmosphere at room temperature. The solution was heated in a 60° C. oil bath and allowed to stir for 2 hours. The resulting mixture was cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 2.7 g (48%) of 3-((t-butyldimethylsilyl)oxy)phenol.

Workup

temperatureThe resulting mixture was cooled to room temperature
customThe reaction was quenched with saturated aqueous ammonium chloride (100 mL)
extractionextracted with ethyl acetate (3×200 mL)
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe resulting crude residue was purified by combiflash (40 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record: ord-a8f318088b80435fb2e086e587c84376
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388153B2

Reaction notes

Loading…