Crotonaldehyde → 3,4-dimethoxy-N-[(E)-5-oxopent-3-enyl]-N-phenyl-benzamide

HRID 2207147Notes

Reaction equation

[CH:1](=[O:5])/C=C/C.[CH2:6]([N:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11](=[O:22])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[CH2:7][CH:8]=[CH2:9]>C(Cl)Cl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C(OC(C)C)=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[O:18][CH3:19])[C:11]([N:10]([CH2:6][CH2:7]/[CH:8]=[CH:9]/[CH:1]=[O:5])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:22]

Participants

Conditions

Temperature: 40 °C

Procedure

Crotonaldehyde (0.5 mL, 3 equiv) was added to a solution of compound 34 (608 mg, 1.95 mmol) in degassed CH2Cl2 (17 mL). Hoveyda-Grubbs' 2nd (31 mg, 2.5% mol) was added and the reaction mixture was heated to 40° C. under Ar atmosphere overnight. The reaction mixture was filtered over Celite and the filtrate was concentrated to dryness. The residue was purified by column chromatography on SiO2 (Petroleum ether/EtOAc=2:3) to afford the title compound 35 as white solid (Yield 644 mg, 97%).

Workup

filtrationThe reaction mixture was filtered over Celite
concentrationthe filtrate was concentrated to dryness
customThe residue was purified by column chromatography on SiO2 (Petroleum ether/EtOAc=2:3)

Sources & evidence

ORD record: ord-195c16f0539b450585eca6accd085c17
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376387B2

Reaction notes

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