Sodium hydride → HCID 70226381, compound

HRID 1532860Notes

Reaction equation

HRID 1532860 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH2:12][OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:31][O:32][C:33](=[O:49])[C:34]1[CH:39]=[CH:38][C:37]([CH2:40]Cl)=[CH:36][C:35]=1[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH3:48]>CN(C=O)C.C(OCC)(=O)C>[CH3:31][O:32][C:33](=[O:49])[C:34]1[CH:39]=[CH:38][C:37]([CH2:40][O:13][CH2:12][C:10]2[O:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)=[CH:36][C:35]=1[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH3:48]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 960786(5-Phenylfuran-2-yl)methanolHCID 206999064-Chloromethyl-2-(2-methylphenyl)benzoic acid methyl ester

Product 1

HCID 70226381HCID 70226381, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 5-phenyl-2-hydroxymethylfuran prepared in Example 327B (345 mg, 1.98 mmol) was dissolved in 5 mL of dry DMF and NaH (50 mg, 1.98 mmol) was added followed by 15-crown-5 (436 mg, 1.98 mmol) and the reaction stirred for 5 minutes at ambient temperature. To the reaction was then added 4-chloromethyl-2-(2-methylphenyl)benzoic acid methyl ester (659 mg, 2.40 mmol) and the reaction was stirred at room temperature for 16 hours. The reaction mixture was taken up in ethyl acetate and washed with water (3×) and brine (3×), dried over Na2SO4, filtered, evaporated and purified by flash chromatography (15% ethyl acetate-hexanes) to give the desired compound (670 mg, 82%) as an oil.

Workup

  1. washwashed with water (3×) and brine (3×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by flash chromatography (15% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-b6f991dada054ef29960b117b34ddea4
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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