Aluminium lithium hydride → 3-(4'-Cyclopentylphenyl)-2-butenol

HRID 1582679Notes

Reaction equation

HRID 1582679 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:25])=[CH:19][C:20](OCC)=[O:21])=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[CH:7]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]([CH3:25])=[CH:19][CH2:20][OH:21])=[CH:16][CH:17]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69907173Ethyl 3-(4-cyclopentylphenyl)but-2-enoate

Product 1

HCID 699071583-(4'-Cyclopentylphenyl)-2-butenolYield 82.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled slurry of LiAlH4 (2.7 g) in dry ether (150 ml) was added a solution of ethyl 3-(4′-cyclopentylphenyl)-but-2-enoate (3a, 8.2 g) in dry ether (50 ml) dropwise. The mixture was stirred at 0° C. for 3 h. The reaction mixture was quenched with water (10 ml). A solution of 10% NaOH (5 ml) was added and then ether layer was decanted. The precipitate was washed with ether and combined organic layer was concentrated. The crude product was purified by column chromatography on silica gel to give 5.6 g (82.3% yield) of 3-(4′-cyclopentylphenyl)-2-butenol (4a, formula 4, R=cyclopentyl) as oil.

Workup

  1. customThe reaction mixture was quenched with water (10 ml)
  2. additionA solution of 10% NaOH (5 ml) was added
  3. customether layer was decanted
  4. washThe precipitate was washed with ether and combined organic layer
  5. concentrationwas concentrated
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-461d66409cb14efc86e72017e20951c7
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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