HCID 20775747, compound → Ethyl 3-methylcyclopent-3-ene-1-carboxylate

HRID 2193930Notes

Reaction equation

HRID 2193930 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([CH2:10][CH:11]=[CH2:12])[CH2:6][C:7](C)=C)[CH3:2]>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][CH:7]=[C:11]([CH3:12])[CH2:10]1)=[O:13])[CH3:2]

Participants

3

Reactant 1

HCID 20775747HCID 20775747, compound

Product 1

HCID 274458Ethyl 3-methylcyclopent-3-ene-1-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a refluxing stirred solution of the 2-Allyl-4-methyl-pent-4-enoic acid ethyl ester (364 mg, 2.0 mmol) in CH2Cl2 (100 mL, 0.02 M solution) was added drop wise a solution of the tricyclohexylphosphine (1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)(benzylidine)ruthenium (IV) dichloride (85 mg, 0.1 mmol) in CH2Cl2 (3.0 mL). After 50 min, the reaction mixture was cooled to room temperature, concentrated and purified on silica gel bond elute using EtOAc/hexane (1:20) as an eluent furnished the 3-Methyl-cyclopent-3-enecarboxylic acid ethyl ester (286 mg, 93% yield) as an oil. 1H NMR (CDCl3, 400 MHz), 5.25 (brs, 1H), 4.17 (q, J=7.1 Hz, 2H), 3.2-3.1 (m, 1H), 2.65-2.46 (m, 4H), 1.74 (s, 3H), 1.28 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified on silica gel bond
  3. washelute

Sources & evidence

ORD record
ord-7ae7a250086f409d8804e1ca81d9d799
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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