Methanol → HCID 19813433, compound

HRID 467094Notes

Reaction equation

HRID 467094 reaction equation
B#B.[CH3:3][C:4]1[C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:16](O)=[O:17].CO>O1CCCC1>[OH:17][CH2:16][C:5]1[O:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=2[C:4]=1[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 361680NSC624898HCID 6328200Diboron2×

Product 1

HCID 19813433HCID 19813433, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 Molar diborane in tetrahydrofuran (18.0 ml, 18.0 mmole) was added dropwise to a suspension of 3-methyl-5-nitrobenzofuran-2-carboxylic acid (1.1 g, 5 mmole) in tetrahydrofuran at 0°. Stirring was continued at 0° for 30 minutes then at room temperature for 18 hours when a second portion of diborane (5.0 ml) was added and the reaction mixture was subjected to ultrasound for 2.5 hours. Methanol was then added cautiously to the reaction mixture and the solvent was removed by evaporation. The residue was taken up in ethyl acetate, washed with aqueous sodium bicarbonate, dried (MgSO4), the solvent removed by evaporation in vacuo and purified by column chromatography on silica eluting with methylene chloride. The product-containing fractions were combined and evaporated to give the title compound, yield 0.96 g. A sample was recrystallised from ethyl acetate, m.p. 149°-150°.

Workup

  1. waitto ultrasound for 2.5 hours
  2. customthe solvent was removed by evaporation
  3. washwashed with aqueous sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation in vacuo
  6. custompurified by column chromatography on silica eluting with methylene chloride
  7. customevaporated

Sources & evidence

ORD record
ord-1c7e2b5eaecc4c2792ab317642a07983
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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