Aluminium lithium hydride → (5-Methoxy-indan-2-yl)-methanol
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.