2-Acetylamino-5-(4,5-dihydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester → 2-Acetylamino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 1894032Notes

Reaction equation

HRID 1894032 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH2:12][CH2:13][CH:14]=2)[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19][C:20](=[O:22])[CH3:21]>C1COCC1.[Ni]>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[C:7]([C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]=1[NH:19][C:20](=[O:22])[CH3:21]

Participants

4

Reactant 1

HCID 585329042-Acetylamino-5-(4,5-dihydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 585329182-Acetylamino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-acetylamino-5-(4,5-dihydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester (13.2 g, 40.1 mmol) in dry THF (250 mL) was shaken under H2 (5 bars) at r.t. in the presence of Raney nickel. (6.0 g, B113W, Degussa) for 46 h. The reaction mixture was then filtered through a sintered funnel and the filtrate was concentrated in vacuo to give the title product (7.5 g, 100%) as a yellow oil. API-ES: m/z 332 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered through a sintered funnel
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a0d0be2767da43529f1869c94cbd10d2
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

Loading…