Water → HCID 57750111, compound

HRID 504536Notes

Reaction equation

HRID 504536 reaction equation
Cl[CH2:2][C:3]#[N:4].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[CH:7]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:2][C:3]#[N:4])=[C:8]([CH:13]2[O:14][CH2:15][CH2:16][O:17]2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 57750166HCID 57750166, compound

Product 1

HCID 57750111HCID 57750111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

At room temperature, 2-chloroacetonitrile (12 g, 0.16 mol) was added into a mixture of 4-chloro-2-[1,3]dioxolan-2-yl-phenol (24.6 g, 0.123 mol) and K2CO3 (34 g, 0.246 mol) in DMF (150 mL). After the reaction mixture was heated at 100° C. for 3 h and cooled to room temperature, water was added. The aqueous phase was extracted with EtOAc twice, washed with saturated K2CO3 solution, water, and dried over anhydrous Na2SO4 to give crude (4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-acetonitrile. The crude product was used for next step without further purification.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous phase was extracted with EtOAc twice
  3. washwashed with saturated K2CO3 solution, water
  4. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-94fa73c01a274b77ac8093a530629a99
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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