Sodium hydride → 4-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester

HRID 1532851Notes

Reaction equation

HRID 1532851 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][OH:9].[CH3:10][O:11][C:12](=[O:28])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][C:14]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27]>CN(C=O)C>[CH3:10][O:11][C:12](=[O:28])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:9][CH2:8][C:4]2[S:3][CH:7]=[CH:6][CH:5]=2)=[CH:15][C:14]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 694672-ThiophenemethanolHCID 234362594-Bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester

Product 1

HCID 702245564-(2-Thienylmethoxymethyl)-2-(2-methylphenyl)benzoic acid methyl esterYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension in DMF (3.5 mL) of sodium hydride (60% in mineral oil, 52 mg, 1.3 mmol) was added 2-thiophenemethanol (0.135 mL, 1.4 mmol) and the reaction mixture was stirred for 1.25 hours. 4-bromomethyl-2-(2-methylphenyl)benzoic acid methyl ester (0.35 mL, 1.2 mmol) was added and the reaction mixture was stirred for 2 hours. The reaction mixture was partitioned between water and ether. The aqueous phase was extracted with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (3% ethyl acetate-hexane) gave 4-(2-thienylmethoxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester (250 mg).

Workup

  1. stirringthe reaction mixture was stirred for 2 hours
  2. customThe reaction mixture was partitioned between water and ether
  3. extractionThe aqueous phase was extracted with ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c2b276c1b084280bf5ea1751b9d0800
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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