Methyl 3-ethylcyclopentane-1-carboxylate → (3-Ethylcyclopentyl)methanol

HRID 1852866Notes

Reaction equation

HRID 1852866 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

HCID 20380553Methyl 3-ethylcyclopentane-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22134208(3-Ethylcyclopentyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe reaction mixture was quenched with saturated Na2SO4
  2. filtrationfiltered through a pad of celite
  3. washwashing with ethyl acetate
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-42fe2ca6b40b4e1ca96588557e8f3151
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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