Sodium borohydride → (2,2,5,5-Tetramethylcyclopentyl)methanol

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Reaction Steps

2,2,5,5-Tetramethylcyclopentane-1-carboxaldehyde is dissolved in 95% ethanol and sodium borohydride is added. After 24 hours, the reaction is quenched with 1M HCl and extracted with ether. The extract is washed, dried over MgSO4 and evaporated to yield 2,2,5,5-tetramethyl-1-cyclopentylmethanol. 2,2,5,5-Tetramethyl-1-cyclopentylmethanol is dissolved in benzene and stirred at 0° C. under argon. A solution of phosphorus tribromide in benzene is added and the mixture is stirred for 2 hours and then heated to 60° C. for 4 hours. The mixture is cooled, poured into ice and extracted with ether. The organic layer is washed and saturated NaHCO3, dried over MgSO4 and evaporated to yield 2,2,5,5-Tetramethyl-1-cyclopentylmethyl bromide.

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