Methanol → HCID 19813433, compound

HRID 345035Notes

Reaction equation

HRID 345035 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-2carboxylic 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-ccfefaa6a927479ca0128388992c8a42
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

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