Water → HCID 69289967, compound

HRID 2415462Notes

Reaction equation

HRID 2415462 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1CCCCC1>[CH2:23]([O:22][C:16](=[O:21])[CH:17]=[C:18]([NH:12][C:11]1[CH:13]=[CH:14][CH:15]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)[CH3:20])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 928923-BenzyloxyanilineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 69289967HCID 69289967, compoundYield 9,987.2%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

20 g (98.4 mmol)of 3-benyloxyaniline, 12.6 ml (0.984 mmol) of ethyl acetoacetate and 0.189 g (1 mmol) of p-toluenesulfonic acid monohydrate in 32 ml of cyclohexane were heated at reflux for 5.5 h in the presence of a water separator funnel. The reaction mixture was cooled to RT, some solid material was filtered off by suction and the filtrate was concentrated in vacuo to give 30.6 g (99%) of the desired 3-(3-benzyloxy-phenylamino)-but-2-enoic acid ethyl ester as a yellow oil. This was used without further purification in the next reaction step.

Workup

  1. filtrationsome solid material was filtered off by suction
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-42968eb1c465498a9393959c562404a7
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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