Aluminium lithium hydride → (4E)-4-Methyl-5-(4-methylphenyl)-4-penten-1-ol

HRID 2408241Notes

Reaction equation

HRID 2408241 reaction equation
[CH3:1]/[C:2](=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)/[CH2:3][CH2:4][C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1]/[C:2](=[CH:9]\[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)/[CH2:3][CH2:4][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58390609Methyl (4E)-4-methyl-5-(4-methylphenyl)-4-pentenoate

Product 1

HCID 67332502(4E)-4-Methyl-5-(4-methylphenyl)-4-penten-1-olYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl (4E)-4-methyl-5-(4-methylphenyl)-4-pentenoate (17.18 g, 0.079 mol) in dry THF (300 ml) was treated, at −78° C. under nitrogen, with solid lithium aluminum hydride (3.15 g, 0.079 mol) in one portion. After 5 minutes the cooling bath was removed and the reaction allowed to reach room temperature and then cooled to 0° C. and treated successively with water (3.15 ml), 5% aqueous sodium hydroxide (9.45 ml) and water (3.15 ml). The reaction was stirred at room temperature for 30 minutes. Anhydrous solid sodium sulfate was added (10 g) and stirring continued for 5 minutes. The solid was filtered off, rinsed with diethyl ether and solvents were removed under vacuum. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 5:1 to 1:1) followed by bulb-to-bulb distillation (120° C./0.001 mbar). 12.54 g (yield=66%) of the desired product were obtained.

Workup

  1. customAfter 5 minutes the cooling bath was removed
  2. customto reach room temperature
  3. additiontreated successively with water (3.15 ml), 5% aqueous sodium hydroxide (9.45 ml) and water (3.15 ml)
  4. additionAnhydrous solid sodium sulfate was added (10 g)
  5. stirringstirring
  6. waitcontinued for 5 minutes
  7. filtrationThe solid was filtered off
  8. washrinsed with diethyl ether and solvents
  9. customwere removed under vacuum
  10. customThe product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 5:1 to 1:1)
  11. distillationfollowed by bulb-to-bulb distillation (120° C./0.001 mbar)

Sources & evidence

ORD record
ord-38dbb95fbcf44dbb804d8ceb7bf3e2ed
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

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