Methyl 3-ethylcyclopentane-1-carboxylate → (3-Ethylcyclopentyl)methanol
Reaction equation
[CH2:1]([CH:3]1[CH2:7][CH2:6][CH:5]([C:8](OC)=[O:9])[CH2:4]1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4]1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of methyl 3-ethylcyclopentanecarboxylate (1.50 g, 9.61 mmol) in THF (10 mL) was added LAH (1 M in THF; 9.6 mL, 9.6 mmol) at 0° C., and the reaction mixture was stirred at 0° C. for 1 hour. The reaction mixture was quenched with saturated Na2SO4, filtered through a pad of celite, washing with ethyl acetate, and the filtrate was concentrated to dryness to afford (3-ethylcyclopentyl)methanol (mixture of cis and trans isomers).
Workup
- customThe reaction mixture was quenched with saturated Na2SO4
- filtrationfiltered through a pad of celite
- washwashing with ethyl acetate
- concentrationthe filtrate was concentrated to dryness
Sources & evidence
- ORD record
- ord-278d1cd89e60435bad5af5d5063aa81c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846657B2
Reaction notes
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