Aluminium lithium hydride → 2,3-Dihydro-5-methoxy-1H-indene-2-methanol

HRID 747972Notes

Reaction equation

HRID 747972 reaction equation
C[O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:15][O:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][CH:5]([CH2:3][OH:2])[CH2:13]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53724337Methyl 5-methoxy-2,3-dihydro-1H-indene-2-carboxylate2×

Product 1

HCID 230442542,3-Dihydro-5-methoxy-1H-indene-2-methanolYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 5-Methoxy-indan-2-carboxylic acid methyl ester (Intermediate 28, 1.90 g, 9.21 mmol), LiAlH4 (0.70 g, 18.43 mmol), and THF anhydrous (60 ml). After the reaction stirs under a nitrogen atmosphere at room temperature for 2 hours, quench the reaction mixture with 5 mL of deionized water. Filter the mixture through a pad of Celite using EtOAc eluent, and wash the organic layer with brine, and dry over Na2SO4. After concentrating under reduced pressure, the flash chromatograph the mixture to afford 1.43 g, 8.0 mmol (87% yield) of the title compound as a clear oil: 1H NMR (500 MHz, CDCl3); 1.4-1.6 (1H, br s), 2.6-2.8 (3H, m), 2.9-3.2 (2H, m), 3.6-3.7 (2H, m), 3.8 (3H, s), 6.7-6.8 (2H, m), 7.1-7.2 (1H, m); TLC 1:1 Hexanes:Ethyl acetate Rf:=0.4.

Workup

  1. customAfter the reaction stirs under a nitrogen atmosphere at room temperature for 2 hours
  2. customquench the reaction mixture with 5 mL of deionized water
  3. filtrationFilter the mixture through a pad of Celite
  4. washwash the organic layer with brine
  5. dry with materialdry over Na2SO4
  6. concentrationAfter concentrating under reduced pressure

Sources & evidence

ORD record
ord-90021a66acf24a73a67f8d2836950091
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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