Methanol → 1-Cyclopropyl-3-(3',4'-dichlorophenyl)-4-nitropentanone

HRID 1415422Notes

Reaction equation

[CH:1]1([C:4](=O)[CH:5]=[CH:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH2:3][CH2:2]1.[N+:16]([CH2:19][CH3:20])([O-:18])=[O:17].[Na].C[OH:23]>>[CH:1]1([CH2:4][C:5](=[O:23])[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH:19]([N+:16]([O-:18])=[O:17])[CH3:20])[CH2:3][CH2:2]1

Participants

Reactant 4

HCID 887Methanol

HCID 6587Nitroethane

HCID 5360545Sodium

HCID 544363412-(3,4-Dichlorophenyl)vinyl cyclopropyl ketone

Product 1

HCID 867344411-Cyclopropyl-3-(3',4'-dichlorophenyl)-4-nitropentanone

Procedure

The procedure of Example IX using 39 g of 1-cyclopropyl-3-(3',4'-dichlorophenyl)prop-2-en-1-one, 15.5 ml of nitroethane and 2 g of sodium in 150 ml of methanol gives 41 g of 1-cyclopropyl-3-(3',4'-dichlorophenyl)-4-nitropentanone as an oily residue which is used in the crude state for the remainder of the operations.

Sources & evidence

ORD record: ord-d3cc967675594c55af3a046ef3f60dcd
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04005103

Reaction notes

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