Benzyl acetoacetate → (E)-3-[4-(2-Hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

HRID 966521Notes

Reaction equation

HRID 966521 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].[C:12]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:17])[CH2:13][C:14]([CH3:16])=O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:19]([O:18][C:12](=[O:17])/[CH:13]=[C:14](/[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[I:11])\[CH3:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 142266Benzyl acetoacetateHCID 223118862-(4-Amino-3-iodophenyl)ethanol

Product 1

HCID 23393857(E)-3-[4-(2-Hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl EsterYield 99.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 4-amino-3-iodophenethyl alcohol from Step A (10 g, 38 mmol) and benzyl acetoacetate (7.3 g, 38 mmol) in benzene (150 mL) was added p-toluenesulfonic acid (361 mg, 1.9 mmol). The mixture was heated at reflux overnight using a Dean Stark condenser. The mixture was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 16.6 g (99%) of the crude desired product as a light brown oil: MS(APCI+): m/z 438.1 (MH+). The compound was taken to Step C without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-881eccce4ea14fafb0eabce0506021a9
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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