N-allyl-N-(4-methoxyphenyl)acrylamide → 1-(4-methoxyphenyl)-1,5-dihydro-2H-pyrrol-2-one

HRID 562578Notes

Reaction equation

HRID 562578 reaction equation
[CH2:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:5](=[O:8])[CH:6]=[CH2:7])C=C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([N:4]2[CH2:1][CH:7]=[CH:6][C:5]2=[O:8])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 67006926N-allyl-N-(4-methoxyphenyl)acrylamide

Product 1

HCID 552671331-(4-methoxyphenyl)-1,5-dihydro-2H-pyrrol-2-oneYield 86%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-allyl-N-(4-methoxyphenyl)acrylamide (150 mg, 0.69 mmol) in degassed methylene chloride (400 mL) was added Grubbs catalyst (58 mg, 0.069 mmol) and the mixture was heated to 40° C. overnight. All volatiles were removed and the resulting material was subjected to flash chromatography (Hexanes:EtOAc 1:1) to yield 1-(4-methoxyphenyl)-1,5-dihydro-2H-pyrrol-2-one (110 mg, 86%).

Workup

  1. customAll volatiles were removed

Sources & evidence

ORD record
ord-98cec8a0e98243c791ffe65931dc643d
Source dataset
uspto-grants-2011_11
Patent number
US08067415B2

Reaction notes

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