تفاعل #946

ord-8bc8a5b260b5493c8773ed6d142bea7c

معادلة التفاعل

[Na+].[OH-]
NaOH
CC=CCC(N)(CC)C(=O)OCC
product
CC=CCC(N)(CC)C(=O)OCC
(+-)-Ethyl 2-amino-2-ethylhex-4-enoate
[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminium hydride
CC=CCC(N)(CC)CO
desired product
المردود 32.5%
CC=CCC(N)(CC)CO
(+-)-2-Amino-2-ethylhex-4-en-1-ol
المردود 32.5%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONWhen addition
  2. 2
    أخرىThe organic phase was separated
  3. 3
    غسيلwashed with brine
  4. 4
    أخرىdried
  5. 5
    أخرىevaporated in vacuo
  6. 6
    workup.DISTILLATIONThe residue was distilled

الإجراء التجريبي

A solution of the product from step (d) (116.7 g) in THF (100 ml) was added to a 1M solution of lithium aluminium hydride in THF (800 ml) at about 0° C. When addition was complete, the mixture was stirred overnight at room temperature, then 50% w/v aqu. NaOH (200 ml) was added. The organic phase was separated, washed with brine, dried and evaporated in vacuo. The residue was distilled to give the desired product as an oil (29.3 g). 1H NMR consistent with the proposed structure.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05723458uspto-grants-1998_03