반응 #78872

반응 방정식

(±)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide

lithium aluminium hydride tetrahydrofuran

→

title compound

수율 76.7%

(±)-[3-(2-Benzyloxy-5-bromophenyl)-3-phenylpropyl]-diisopropylamine

수율 76.7%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction was refluxed for 4 hrs
2. 2
   기타quenched with the dropwise addition of water
3. 3
   기타After removal of the precipitate the solvent
4. 4
   기타was evaporated
5. 5
   workup.DISSOLUTIONthe oily residue dissolved in diluted sulphuric acid
6. 6
   세척The aqueous phase was washed several times with diethyl ether
7. 7
   추출extracted with diethyl ether
8. 8
   건조The extract was dried (sodium sulphate)
9. 9
   여과filtered
10. 10
    기타evaporated to dryness in vacuum

실험 절차

To a stirred solution of (±)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropionamide (11.8 g) in 40 ml of dry tetrahydrofuran was added 1 M lithium aluminium hydride/tetrahydrofuran (36 ml). The reaction was refluxed for 4 hrs and then quenched with the dropwise addition of water. After removal of the precipitate the solvent was evaporated and the oily residue dissolved in diluted sulphuric acid. The aqueous phase was washed several times with diethyl ether, adjusted to pH 10-12 (aqueous NaOH), and extracted with diethyl ether. The extract was dried (sodium sulphate), filtered and evaporated to dryness in vacuum to leave 8.1 g (76.7%) of the title compound as a viscous colourless oil, tlc: (4) 0.86. The NMR spectrum corresponds to the product, obtained from the tosylate precursor (see above).

출처