2-Cyclopenten-1-one → Phenylcyclopentadiene

HRID 2188195Notes

Reaction equation

HRID 2188195 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]1([Li])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[C:7]1([C:5]2[CH2:4][CH:3]=[CH:2][CH:1]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 178506676HCID 178506676, compound

Product 1

HCID 244167PhenylcyclopentadieneYield 120.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

100 ml (1.2 mol) of 2-cyclopenten-1-one in 400 ml of diethyl ether are added dropwise to 2.3 mol of phenyllithium in 1000 ml of diethyl ether at −5° C. After hydrolysis and extraction of the aqueous phase with the diethyl ether, the combined organic phases are dried over sodium sulfate. After the solvent has been stripped off, 205 g of crude product are obtained. The product is heated to 180° C. for three hours in a vigorous argon stream in a

Workup

  1. dry with materialthe combined organic phases are dried over sodium sulfate

Sources & evidence

ORD record
ord-3a9c9b5d0beb47d18269cf3abb125710
Source dataset
uspto-grants-2002_06
Patent number
US06410661B1

Reaction notes

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