Chloromethyl Methyl Ether → 2,5-Diphenyl-3-(methoxymethoxy)-thiophene

HRID 359148Notes

Reaction equation

HRID 359148 reaction equation
[C:1]1([C:7]2[S:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:11]=2[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:21][O:22][CH2:23]Cl.CCOCC.O>CN(C)C=O>[C:1]1([C:7]2[S:8][C:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:10][C:11]=2[O:12][CH2:21][O:22][CH3:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 150787382,5-Diphenylthiophene-3-olHCID 21584184Diethylether water

Product 1

HCID 150787402,5-Diphenyl-3-(methoxymethoxy)-thiopheneYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, ice cooled solution of 2,5-diphenyl-3-hydroxythiophene (0.12 g, 0.5 mmol) in dried N,N-dimethylformamide (2 ml) was added sodium hydride (30 mg of a 60% suspension in mineral oil). When the initial vigorous reaction subsides (ca. 4 minutes), the mixture was allowed to stir at ambient temperatures for 20 minutes and then recooled. Chloromethyl methyl ether (0.055 ml, 0.7 mmol) was then added all at once. After stirring cold for ca. 30 minutes, the mixture was allowed to stir at ambient temperatures for ca. 4 hours and then added to a stirred ether/water mixture. The ether layer was washed 3 times with water, dried over sodium sulfate, filtered, concentrated to a residue, and chromatographed on silica gel (methylene chloride/hexane), to yield 0.13 g of (II). M.S.: M+ =296; NMR: consistent. ##STR27##

Workup

  1. customWhen the initial vigorous reaction subsides (ca. 4 minutes)
  2. stirringAfter stirring cold for ca. 30 minutes
  3. stirringto stir at ambient temperatures for ca. 4 hours
  4. washThe ether layer was washed 3 times with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a residue
  8. customchromatographed on silica gel (methylene chloride/hexane)

Sources & evidence

ORD record
ord-8ebe84a4a2734710adc20aa22273e31b
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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