تفاعل #218952

معادلة التفاعل

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

lithium aluminium hydride tetrahydrofuran

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title compound

المردود 76.7%

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

المردود 76.7%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was refluxed for 4 hrs
2. 2
   أخرىquenched with the dropwise addition of water
3. 3
   أخرىAfter removal of the precipitate the solvent
4. 4
   أخرىwas evaporated
5. 5
   workup.DISSOLUTIONthe oily residue dissolved in diluted sulphuric acid
6. 6
   غسيلThe aqueous phase was washed several times with diethyl ether
7. 7
   استخلاصextracted with diethyl ether
8. 8
   تجفيفThe extract was dried (sodium sulphate)
9. 9
   ترشيحfiltered
10. 10
    أخرىevaporated to dryness in vacuum

الإجراء التجريبي

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).

المصدر