Aluminium lithium hydride → (4-tert-Butyl-3-isopropylphenyl)methanol

HRID 1675255Notes

Reaction equation

HRID 1675255 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][C:6]=1[CH:15]([CH3:17])[CH3:16])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([C:5]1[CH:14]=[CH:13][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[CH:15]([CH3:17])[CH3:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59300556Methyl 4-tert-butyl-3-isopropylbenzoate

Product 1

HCID 59300613(4-tert-Butyl-3-isopropylphenyl)methanolYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the ester 26.3 (145 mg, 0.62 mmol) in anhydrous THF (5.0 mL) was added dropwise 1.0 M LiAlH4 in THF (1.2 mL, 1.20 mmol) at 0° C. The resulting mixture was stirred for 5 minutes. The reaction was slowly quenched with 1 N NaOH aqueous solution (3.00 mL). The mixture was extracted with EtOAc (10 mL), dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (0-10% EtOAc/hexane) to give 26.4 (77 mg, 60%) as a clear oil.

Workup

  1. customThe reaction was slowly quenched with 1 N NaOH aqueous solution (3.00 mL)
  2. extractionThe mixture was extracted with EtOAc (10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography on silica gel (0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-9c5deb1f37154befbf002500a2f7b099
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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