Chloromethyl Methyl Ether → HCID 67811781, compound

HRID 244946Notes

Reaction equation

HRID 244946 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:15][N:16]([C:19]([CH3:29])([CH3:28])[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[C:17]=2[OH:18])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[CH3:37][O:38][CH2:39]Cl>CN(C)C=O.C(OCC)C>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:15][N:16]([C:19]([CH3:28])([CH3:29])[CH2:20][C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)[C:17]=2[O:18][CH2:37][O:38][CH3:39])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 178442350HCID 178442350, compound

Product 1

HCID 67811781HCID 67811781, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

152 mg (0.329 mol) of ethyl 4-(4-hexylphenyl)-5-hydroxy-1-(2-methyl-1-(p-tolyl)propan-2-yl)-1H-pyrazole-3-carboxylate was dissolved in 1.6 mL of N,N-dimethylformamide, mixed with 26 mg (0.65 mmol) of 60 wt % sodium hydride (suspended in mineral oil) and 0.050 mL (0.66 mmol) of chloromethyl methyl ether under cooling with ice successively and stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was diluted with diethyl ether and washed with 1 M hydrochloric acid, with saturated aqueous sodium hydrogen carbonateand with saturated aqueous sodium chloride successively. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give the desired product (crude yield 174 mg).

Workup

  1. temperatureunder cooling with ice successively
  2. customAfter completion of the reaction
  3. washwashed with 1 M hydrochloric acid, with saturated aqueous sodium hydrogen carbonateand with saturated aqueous sodium chloride successively
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2dc4019f1f24d7baeecf24eb9e1108a
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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