Alpha-Cyano-4-Hydroxycinnamic Acid → HCID 68639232, compound

HRID 643193Notes

Reaction equation

HRID 643193 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5])#[N:2].C(N(CC)CC)C.[C:22]([O:26][C:27](OC([O-])=O)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(#N)C.CN(C)C1C=CN=CC=1>[C:1]([C:3](=[CH:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])=[CH:12][CH:13]=1)[C:4]([OH:6])=[O:5])#[N:2]

Participants

6

Reactant 3

HCID 2102Alpha-Cyano-4-Hydroxycinnamic AcidHCID 8471TriethylamineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 68639232HCID 68639232, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

5.6 g (30 mmol) of 2-cyano-3-(4-hydroxyphenyl) acrylic acid dissolved in 40 ml acetonitrile were stirred with 4.6 ml (33 mmol) of triethylamine until a clear solution was obtained. 0.2 g (4 mmol) 4-dimethylaminopyridine and 7.3 g (33 mmol) tert-butylpyrocarbonate were then added to the clear solution. After 2 hours reaction (the solution is at that point colourless), the solution was reduced to its half volume and washed with 200 ml of a cold 5% citric acid solution.

Workup

  1. customwas obtained
  2. customAfter 2 hours reaction (the solution
  3. washwashed with 200 ml of a cold 5% citric acid solution

Sources & evidence

ORD record
ord-a1e1ef0c4a5f408ca79e1e3406d0c137
Source dataset
uspto-grants-2010_04
Patent number
US07700306B2

Reaction notes

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