Aluminium lithium hydride → (4-Cyclopropylphenyl)methanol

HRID 1351532Notes

Reaction equation

HRID 1351532 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:11]1([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23577288Ethyl 4-cyclopropylbenzoate

Product 1

HCID 22135711(4-Cyclopropylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

4-Cyclopropyl-benzoic acid ethyl ester (2.46 g, 13 mmol), and THF (250 mL) were combined under nitrogen and cooled in an IPA/dry ice bath to −70° C. Lithium aluminum hydride solution (20 mL, 20 mmol, 1.0M) was added dropwise. After 2 h excess lithium aluminum hydride was quenched by adding EtOAc dropwise. The reaction was warmed to 25° C., then the solvent was removed in vacuo. Water (200 mL) and a few drops of HCl (aq, 6N) were added. The mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine, dried with NA2SO4 and filtered. The filtrate was removed in vacuo and the remaining residue was purified by flash column chromatography (hexane:EtOAc 40:60) to give (4-cyclopropyl-phenyl)-methanol as a colorless oil.

Workup

  1. customAfter 2 h excess lithium aluminum hydride was quenched
  2. additionby adding EtOAc dropwise
  3. temperatureThe reaction was warmed to 25° C.
  4. customthe solvent was removed in vacuo
  5. additionWater (200 mL) and a few drops of HCl (aq, 6N) were added
  6. extractionThe mixture was extracted with EtOAc (3×100 mL)
  7. washThe combined organic extracts were washed with brine
  8. customdried with NA2SO4
  9. filtrationfiltered
  10. customThe filtrate was removed in vacuo
  11. customthe remaining residue was purified by flash column chromatography (hexane:EtOAc 40:60)

Sources & evidence

ORD record
ord-5fb14f623a924ba1b77ffec057300c7d
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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