Chloromethyl ethyl ether → HCID 21459514, compound

HRID 372950Notes

Reaction equation

HRID 372950 reaction equation
[N+:1]([C:4]1[NH:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].CC(C)([O-])C.[K+].Cl[CH2:18][O:19][CH2:20][CH3:21]>C1COCC1.CCOCC.O>[CH2:20]([O:19][CH2:18][N:8]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[C:7]1[C:9]#[N:10])[CH3:21]

Participants

7

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 214595565-Nitro-1H-pyrrole-2-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 21459514HCID 21459514, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 560 mg of 5-nitropyrrole-2-carbonitrile (4 mmol) in 20 mL of dry THF, is added 515 mg of potassium tert-butoxide (4.6 mmol). After the addition of 0.45 mL of chloromethylethylether (4.8 mmol) to the mixture, the mixture is stirred for 4 hours, then diluted with ether (30 mL) and water (50 mL). The organic layer is separated, washed with water MgSO4 (20 mL) and dried over MgSO4. After evaporation of the solvent a red oil is obtained (600 mg, 75%) 1-(ethoxymethyl)-5-nitropyrrole-2-carbonitrile.

Workup

  1. customThe organic layer is separated
  2. washwashed with water MgSO4 (20 mL)
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the solvent a red oil

Sources & evidence

ORD record
ord-3f412b9c552c4276a75efb9679699cdc
Source dataset
uspto-grants-1992_11
Patent number
US05162308

Reaction notes

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