Norborn-2-ylacetic acid → 2-(Bicyclo(2.2.1)heptan-2-yl)ethan-1-ol
Reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9](O)=[O:10].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9][OH:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Norbornane acetic acid (15 g, 97 mmol) was dissolved in anhydrous tetrahydrofuran (150 mL) and treated dropwise with lithium aluminum hydride (195 mL, 1 M in tetrahydrofuran) at 0° C. The reaction was stirred for three days then quenched by dropwise addition of water (50 mL). The reaction was diluted with diethyl ether (300 mL) and washed with water (3×200 mL). The combined organic phases were dried (MgSO4), filtered, and concentrated to yield an oil. The product was passed through a pad of silica gel to yield 2-bicyclo[2.2.1]hept-2-yl-ethanol as a colorless oil (13.1 g, 96%).