Potassium Iodide → Dimethyl 2-(4-benzyloxyphenoxy)malonate

HRID 1260504Notes

Reaction equation

HRID 1260504 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:17]([C:22]([O:24][CH3:25])=[O:23])[C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:17]([C:22]([O:24][CH3:25])=[O:23])[C:18]([O:20][CH3:21])=[O:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7638MonobenzoneHCID 10796Cesium carbonateHCID 120070Dimethyl chloromalonate2×

Product 1

HCID 67071604Dimethyl 2-(4-benzyloxyphenoxy)malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Benzyloxyphenol (1.0 g, 4.99 mmol), dimethyl 2-chloromalonate (998.2 mg, 5.99 mmol), cesium carbonate (3.25 g, 9.99 mmol) and potassium iodide (41.45 mg, 0.25 mmol) were stirred in 50 ml of DMF at 60° C. for 1.5 h. Addition of 200 μl of dimethyl 2-chloromalonate was followed by stirring at 60° C. for 1 h and at 80° C. for 1 h and concentration, and the residue was taken up in ethyl acetate and water. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 477 mg (29%), M+H+: 331.18.

Workup

  1. concentrationconcentration
  2. customThe organic phase was separated off
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-c409f6345dc04e14979dfbd926bc78a7
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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