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

HRID 2118470Notes

Reaction equation

HRID 2118470 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[CH:9]=[O:10].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:11])[CH2:6][CH2:5][C:4]([CH3:7])([CH3:8])[CH:3]1[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 9793878Cyclopentanecarboxaldehyde, 2,2,5,5-tetramethyl-

Product 1

HCID 13629260(2,2,5,5-Tetramethylcyclopentyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. customthe reaction is quenched with 1M HCl
  2. extractionextracted with ether
  3. washThe extract is washed
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-5022b280acae4195be37becb993671ee
Source dataset
uspto-grants-1987_07
Patent number
US04678675

Reaction notes

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