Ethyl 4-decenoate, (4E)- → Dec-4-en-1-ol

HRID 530169Notes

Reaction equation

HRID 530169 reaction equation
[C:1](OCC)(=[O:11])[CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([OH:11])[CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 5362583Ethyl 4-decenoate, (4E)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 5702619Dec-4-en-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution (0° C.) of (E)-ethyl dec-4-enoate (20 g, 101 mmol) in anhydrous diethyl ether (350 mL) was added lithium aluminum hydride (8.9 g, 212 mmol) under nitrogen. The solution was stirred for 1 hour at room then cooled to 0° C. and quenched slowly with 5M NaOH (30 mL) and diluted with ethyl ether (100 mL). The solution was stirred for 30 min and dried on magnesium sulfate, filtered and concentrated vacuo to dryness to afford (E)-dec-4-en-1-ol 84 as oil (16.1 g, quantitative).

Workup

  1. customquenched slowly with 5M NaOH (30 mL)
  2. additiondiluted with ethyl ether (100 mL)
  3. stirringThe solution was stirred for 30 min
  4. customdried on magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated vacuo to dryness

Sources & evidence

ORD record
ord-54244bdd06fa41629dc906aee4e01597
Source dataset
uspto-grants-2016_05
Patent number
US09352042B2

Reaction notes

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