Sodium Hydroxide → (+-)-2-Amino-2-ethylhex-4-en-1-ol

HRID 850

Reaction equation

HRID 850 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

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54508860(+-)-Ethyl 2-amino-2-ethylhex-4-enoate

Product 1

HCID 54018667(+-)-2-Amino-2-ethylhex-4-en-1-olYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. additionWhen addition
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated in vacuo
  6. distillationThe residue was distilled

Sources & evidence

ORD record
ord-8bc8a5b260b5493c8773ed6d142bea7c
Source dataset
uspto-grants-1998_03
Patent number
US05723458

Linked notes

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