2-Cyclopenten-1-one → 1-Butylcyclopentanol

HRID 1261571Notes

Reaction equation

HRID 1261571 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[C:6]1(=[O:11])[CH2:10][CH2:9][CH:8]=[CH:7]1.[NH4+].[Cl-]>O>[CH2:2]([C:6]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 135882-Cyclopenten-1-oneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 1370191-ButylcyclopentanolYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

nBuLi (1.00 mL; 1.50 mmol; 1.00 equiv) was added to a solution of cyclopentenone (84 mg; 1.0 mmol) in the presence of LaCl3.2LiCl (0.33 M; 3.03 mL, 1.00 mmol, 1.00 equiv) at 0° C. After 2 min, sat. aq. NH4Cl (2 mL) and water (2 mL) was added and the aqueous layer was extracted with ether (4×10 mL). The combined extracts were dried (Na2SO4). Careful evaporation under reduced pressure afforded analytically clean 1-butylcyclopentanol (8) as colorless oil (139 mg, 98%). The analytical data were found to be in accordance with the literature data.

Workup

  1. customat 0° C
  2. extractionthe aqueous layer was extracted with ether (4×10 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customCareful evaporation under reduced pressure

Sources & evidence

ORD record
ord-3f6edf96eb8649acb76b371289dccd0b
Source dataset
uspto-grants-2013_06
Patent number
US08470982B2

Reaction notes

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