Chloromethyl Methyl Ether → HCID 68194700, compound

HRID 1626794Notes

Reaction equation

HRID 1626794 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19][O:20][CH2:21]Cl.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14][CH2:19][O:20][CH3:21])=[CH:9][CH:8]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68193194HCID 68193194, compound

Product 1

HCID 68194700HCID 68194700, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[4-(4-Bromobenzyl)phenyl]methanol (2.7 g, 9.6 mmol) was dissolved in tetrahydrofuran (50 mL), and sodium hydride (55%, 0.50 g, 12 mmol) was added at 0° C., followed by stirring at the same temperature for 30 minutes under a nitrogen atmosphere. To the reaction solution at 0° C. was added dropwise a solution of chloromethyl methyl ether (1.0 g, 13 mmol) in tetrahydrofuran (10 mL), followed by stirring at room temperature for 4 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.55 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (2.5 g, 7.8 mmol) as a colorless oil (yield 81%).

Workup

  1. stirringby stirring at room temperature for 4 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  6. concentrationa fraction corresponding to the Rf value=0.55 (hexane/ethyl acetate=4/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bdf46c681e714cd6953ce376652b3895
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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