Water → 2-Isobutylpent-4-en-1-ol

HRID 551638Notes

Reaction equation

HRID 551638 reaction equation
[CH2:1]([CH:5]([CH2:9][CH:10]=[CH2:11])[C:6](O)=[O:7])[CH:2]([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([CH:5]([CH2:9][CH:10]=[CH2:11])[CH2:6][OH:7])[CH:2]([CH3:4])[CH3:3]

Participants

6

Procedure

2-isobutyl-4-pentenoic acid (J. Am. Chem. Soc. 115, 1993, 8669) (13 g, 83 mmol) was dissolved in tetrahydrofuran (80 mL), and the solution was added dropwise to a tetrahydrofuran (80 mL) mixed solution of lithium aluminum hydride (3.4 g, 90 mmol) under ice cooling. The mixture was stirred at this temperature for 1 hour. Then, water (3.4 mL), a 15% aqueous sodium hydroxide solution (3.4 mL), and water (10.2 mL) were added thereto in this order, and the mixture was stirred overnight. After removal of insoluble matter, the filtrate was concentrated to obtain the compound of interest as an oil substance (4.9 g, 42%).

Workup

  1. stirringin this order, and the mixture was stirred overnight
  2. customAfter removal of insoluble matter
  3. concentrationthe filtrate was concentrated
  4. customto obtain the compound of interest as an oil substance (4.9 g, 42%)

Sources & evidence

ORD record
ord-91bb5a849bba4df89c330b3a5f1fd770
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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