Sodium hydride → Ethyl acetate hexane

HRID 1166949Notes

Reaction equation

HRID 1166949 reaction equation
[H-].[Na+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7](O)=[CH:6][C:5]=2[O:4]1.[CH:13]1C=CN(S(C2C=CSC=2CBr)(=O)=O)C=1>CN(C=O)C.O>[CH3:7][CH2:6][CH2:5][CH2:10][CH2:9][CH3:8].[CH3:10][CH2:5][O:4][C:3]([CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 68289SesamolHCID 23445314HCID 23445314, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (100 mg, 5 mmole) was added to a stirred solution of 3,4-methylenedioxyphenol (0.607 g, 4.5 mmol) in DMF (dry, 5 ml) at 0° C. under a nitrogen atmosphere with stirring. The reaction mixture was permitted to attain room temp and stirring continued for 1 hr. The reaction mixture was cooled to 0° C. and N-[(2-bromomethyl)thiophene-3-sulfonyl]pyrrole was added. Stirring was continued at ambient temperature for 16 hr. The reaction mixture was diluted with water (100 ml), extracted with ethyl acetate (2×50 ml) and washed with 1N NaOH (2×25 ml) to remove phenol derivative. The mixture was dried over MgSO4 and concentrated resulting in N-{2-[(3,4-methylenedioxy)phenoxymethyl]thiophene-3-sulfonyl}pyrrole, which was recrystallized using hexane/EtOAc (1.0 g, 92% yield).

Workup

  1. customto attain room temp
  2. stirringstirring
  3. stirringStirring
  4. waitwas continued at ambient temperature for 16 hr
  5. extractionextracted with ethyl acetate (2×50 ml)
  6. washwashed with 1N NaOH (2×25 ml)
  7. customto remove phenol derivative
  8. dry with materialThe mixture was dried over MgSO4
  9. concentrationconcentrated
  10. customresulting in N-{2-[(3,4-methylenedioxy)phenoxymethyl]thiophene-3-sulfonyl}pyrrole
  11. customwhich was recrystallized

Sources & evidence

ORD record
ord-238ed2de9b4148efaa149d1d27ea2ea4
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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