Acetone → HCID 21217924, compound

HRID 1586223Notes

Reaction equation

HRID 1586223 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([OH:14])[CH2:10][C:11]([O-:13])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH:15]1[C:20]([CH2:21]Br)=[CH:19][CH:18]=[C:17]([C:23]#[N:24])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[CH3:33][C:34](C)=O>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([O:14][CH2:21][C:20]2[CH:19]=[CH:18][C:17]([C:23]#[N:24])=[CH:16][CH:15]=2)[CH2:10][C:11]([O:13][CH2:33][CH3:34])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 5

HCID 180AcetoneHCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 869964-(Bromomethyl)benzonitrileHCID 21217956HCID 21217956, compound

Product 1

HCID 21217924HCID 21217924, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Part B. The 3-(cyano)-beta-(hydroxy)benzenepropanoate (0.33 gm, 1.51 mmol), a-bromo p-tolunitrile (0.59 gm, 3.0 mmol), cesium carbonate (0.74 gm, 2.26 mmol) and catalytic amount of potassium iodide were combined in 10 mLs acetone under a nitrogen atmosphere. The reaction was heated to reflux for 21/2 days, allowed to cool, was diluted with ethyl acetate and the solids were filtered off. The filtrate was concentrated to give a crude yellow oil. The product was purified by flash chromatography on silica gel (200 mLs) eluting toluene:ethyl acetate (v:v, 90:10) to give the ethyl 3-(cyano)-beta-[(4cyanophenyl)methoxy]benzenepropanoate as a viscous oil 0.25 gm (50%). MS 352(M+NH4). 1H NMR (CDCl3); 7.7-7.35(m, 8H), 4.92(dd, 1H), 4.45(dd, 2H), 4.15(m, 2H), 2.85(dd, 1H), 2.60(dd, 1H), 1.20(t,3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 21/2 days
  3. temperatureto cool
  4. filtrationthe solids were filtered off
  5. concentrationThe filtrate was concentrated
  6. customto give a crude yellow oil
  7. customThe product was purified by flash chromatography on silica gel (200 mLs)
  8. washeluting toluene

Sources & evidence

ORD record
ord-c059b6df10f64a83a11e7e0356f7d1f1
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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