TBDMS protection of 2,5-hydroxybenzaldehyde

SyntheticPage 661
Published Jul 29, 2013


Reaction Scheme

Procedure

To a solution of 2,5-hydroxybenzaldehyde (1.24 g, 8.97 mmol) in dry dichloromethane (20 cm3) were added TBDMSCl (1.35 g , 8.97 mmol) and imidazole. (0.61 g, 8.97 mmol) The mixture was stirred overnight and filtered to remove all insoluble material. All volatiles were removed under reduced pressure and the remaining solid (88% purity by 1H NMR) recrystallised from hot hexanes. (1.40 g, 62%)

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