Dimethyl Carbonate → HCID 22282423, compound

HRID 717527Notes

Reaction equation

HRID 717527 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[C:9]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])(=[O:11])[CH3:10]>C1(C)C=CC=CC=1>[C:15]([C:14]1[CH:13]=[C:12]([C:9](=[O:11])[CH2:10][C:3]([O:6][CH3:7])=[O:8])[CH:19]=[CH:18][CH:17]=1)#[N:16]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 802223-Acetylbenzonitrile

Product 1

HCID 22282423HCID 22282423, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a three-necked flask equipped with an argon inlet and a condenser were placed sodium hydride (60%, 689.5 mg, 17.23 mmol), dimethyl carbonate (1.55 g, 17.23 mmol) and 15 mL of toluene. The mixture was stirred under reflux and a solution of 3-acetylbenzonitrile (1.0 g, 6.19 mmol) in toluene (15 mL) was added drop wise. The reaction mixture was stirred at 100° C. for 2 h. The reaction mixture was monitored by LCMS and purified by column chromatography on silica gel eluted with 0-10% of ethyl acetate in petroleum ether to give the product (1.2 g, 86%).

Workup

  1. customInto a three-necked flask equipped with an argon inlet and a condenser
  2. temperatureunder reflux
  3. stirringThe reaction mixture was stirred at 100° C. for 2 h
  4. custompurified by column chromatography on silica gel
  5. washeluted with 0-10% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-4ef76abcf3a4401da9b62f9194b305c3
Source dataset
uspto-grants-2015_11
Patent number
US09193710B2

Reaction notes

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