Acetic Acid → Diisopropylether ethyl acetate

HRID 397888Notes

Reaction equation

HRID 397888 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[Cl:10])[NH2:6].[CH:13]([O:20][CH2:21][CH3:22])(OCC)OCC.[N+:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([O-])=O.[C:32]([OH:35])(=O)[CH3:33]>[Fe]>[Cl:10][C:9]1[CH:8]=[CH:7][C:5]([N:6]2[CH:32]=[C:22]([CH2:21][OH:20])[N:23]=[CH:26]2)=[CH:4][C:3]=1[C:2]([F:1])([F:11])[F:12].[CH3:31][CH2:30][O:29][C:27]([CH3:26])=[O:28].[O:35]([CH:8]([CH3:7])[CH3:9])[CH:32]([CH3:33])[CH3:13]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 69379Ethyl nitroacetate

Product 2

HCID 22281796Diisopropylether ethyl acetateHCID 23444982HCID 23444982, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

3-Trifluoromethyl-4-chloroaniline was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The isolated acid was directly reduced with BH3 THF complex followed by hydrolytic workup and the title compound, Mp. 148-153° C. (AcOEt/iPr2O), MS: m/e=276 (M+), was obtained as a white crystalline solid.

Sources & evidence

ORD record
ord-820032531a414473b4e9c46fd13bb26c
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

Loading…