The hazardous and inconvenient Schmidt procedure for tert-butyl benzoate ester cleavage by NaH in DMF has been reinvestigated. The reaction is suggested to involve B(AC)2 ester cleavage, facilitated by adventitious, NaH-derived NaOH, rather than the proposed E2 elimination of isobutylene by DMF-derived NaNMe(2). Powdered KOH in THF is a significantly safer and simpler alternative that effects cleavage of tert-butyl benozoates, at ambient temperature, in excellent yield (94-99%).
|Number of pages||4|
|Journal||Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry|
|Publication status||Published - 22 Jan 2009|
- tert-butyl esters
- SODIUM HYDRIDE