4,4,4-Trifluoro-but-2-ynoic acid benzyl ester → (E)-4,4,4-Trifluoro-3-[4-(2-hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

HRID 966479Notes

Reaction equation

HRID 966479 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[I:11].[CH2:12]([O:19][C:20](=[O:27])[C:21]#[C:22][C:23]([F:26])([F:25])[F:24])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:12]([O:19][C:20](=[O:27])/[CH:21]=[C:22](/[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[I:11])\[C:23]([F:26])([F:25])[F:24])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 145682614,4,4-Trifluoro-but-2-ynoic acid benzyl esterHCID 223118862-(4-Amino-3-iodophenyl)ethanol

Product 1

HCID 23393858(E)-4,4,4-Trifluoro-3-[4-(2-hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl EsterYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4-Amino-3-iodo-phenyl)-ethanol (6.0 g, 23 mmol, 1.0 eq) was added to the solution of the 4,4,4-trifluoro-but-2-ynoic acid benzyl ester (5.7 g, 25 mmol, 1.1 eq) obtained from previous step in methanol (20 mL) at room temperature. The reaction mixture was stirred for 1 hour. After the solvent was removed, the residue was purified by flash chromatography (SiO2, hexanes-ethyl acetate) to yield 9.5 g of the desired enamine as pale yellow liquid (84.0% yield).

Workup

  1. customAfter the solvent was removed
  2. customthe residue was purified by flash chromatography (SiO2, hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-5de49cb1dd1a43cd938b354f8825e029
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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