Water → HCID 18433855, compound

HRID 2187318Notes

Reaction equation

HRID 2187318 reaction equation
[CH:1]1([CH:6]([CH3:12])[CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:13][Li].O>C(OCC)C>[CH:1]1([CH:6]([CH3:12])[CH2:7][CH2:8][C:9](=[O:11])[CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 2288754-cyclopentylpentanoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 18433855HCID 18433855, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

4-Cyclopentylpentanoic acid (3.4 g; 20 mmol; prepared in example 6) in diethyl ether (90 ml) was added at 0° C. to 1.6 M diethyl ether solution of methyllithium (25 ml; 40 mmol), and diluted with the same solvent (75 ml). After 3.5 hours stirring at 5° C., water (100 ml) was added, and the separated organic layer was washed with brine (3×400 ml), dried (MgSO4), concentrated in vacuo, and bulb-to-bulb distilled (125° C./0.2 torr) to give 1.8 g (53.5% yield) of 5-cyclopentylhexan-2-one.

Workup

  1. washthe separated organic layer was washed with brine (3×400 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo, and bulb-to-bulb
  4. distillationdistilled (125° C./0.2 torr)

Sources & evidence

ORD record
ord-52a4d48f96714d0ea72b3b9433c353c2
Source dataset
uspto-grants-2002_06
Patent number
US06410000B1

Reaction notes

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