Tetrahydrofuran → HCID 24795835, compound

HRID 2273836Notes

Reaction equation

HRID 2273836 reaction equation
[CH:1](/[C:4](=[CH:8]\[CH:9]=[C:10]([CH3:12])[CH3:11])/[C:5](O)=[O:6])([CH3:3])[CH3:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O.C(OCC)(=O)C>[CH:1](/[C:4](=[CH:8]\[CH:9]=[C:10]([CH3:12])[CH3:11])/[CH2:5][OH:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 118037477HCID 118037477, compound

Product 1

HCID 24795835HCID 24795835, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a nitrogen atmosphere, a mixture of 48.1 g of 2-isopropyl-5-methyl-2,4-hexadienoic acid (2) having a purity of 98.0% and an (E)-isomer purity of 98.1% and 300 ml of tetrahydrofuran was added dropwise to a mixture of 20.0 g of lithium aluminum hydride and 500 ml of tetrahydrofuran over 70 minutes, which was stirred under ice cooling. The reaction mixture was stirred under ice cooling for 30 minutes and then stirred at room temperature for 17.5 hours, and subjected to careful and sequential additions of 50 g of ethyl acetate, 20.7 g of water, 12.42 g of 25% aqueous sodium hydroxide solution, and 70.38 g of water. The crystals thus formed were filtered. The filtrate was dried and concentrated to obtain 54.99 g of crude intended product having a purity of 76.8% and containing 16.4% of the solvent. The yield was 98%.

Workup

  1. stirringThe reaction mixture was stirred under ice cooling for 30 minutes
  2. stirringstirred at room temperature for 17.5 hours
  3. customThe crystals thus formed
  4. filtrationwere filtered
  5. customThe filtrate was dried
  6. concentrationconcentrated
  7. customto obtain 54.99 g of crude

Sources & evidence

ORD record
ord-25e843d93a3645d694c6711dda2badd3
Source dataset
uspto-grants-2015_09
Patent number
US09126923B2

Reaction notes

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