Sodium Hydroxide → (+-)-2-Amino-2-ethylhex-4-en-1-ol
Reaction equation
[NH2:1][C:2]([CH2:12][CH3:13])([CH2:8][CH:9]=[CH:10][CH3:11])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[NH2:1][C:2]([CH2:12][CH3:13])([CH2:8][CH:9]=[CH:10][CH3:11])[CH2:3][OH:4]Participants
5
Procedure
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.
Workup
- additionWhen addition
- customThe organic phase was separated
- washwashed with brine
- customdried
- customevaporated in vacuo
- distillationThe residue was distilled
Sources & evidence
- ORD record
- ord-8bc8a5b260b5493c8773ed6d142bea7c
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723458
Reaction notes
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