Methanol → HCID 23320881, compound

HRID 280626Notes

Reaction equation

HRID 280626 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](O)=[O:11])=[C:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1.CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH2:13][CH3:14])[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 2332089186793-66-0

Product 1

HCID 23320881HCID 23320881, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5-bromo-3-ethylbenzofuran-2-carboxylic acid (1.91 g) in dry tetrahydrofuran (70 ml) at 0° C. under an atmosphere of dry nitrogen was added dropwise borane-tetrahydrofuran complex (25 ml of 1M solution). The solution was stirred at 0° C. for 1 hour and then at room temperature for 24 hours. Methanol was added continuously to decompose the excess borane complex and then the solution was evaporated. The residue was dissolved in ether and the solution was washed with water and dried (Na2SO4). Evaporation of the ether gave a solid which was chromatographed on silica gel. Elution with chloroform gave a solid which was crystallised from ethyl acetate/petrol to give 5-bromo-3-ethyl-2-hydroxymethylbenzofuran (1.05 g), m.p. 93°-94°.

Workup

  1. waitat room temperature for 24 hours
  2. customthe solution was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washthe solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the ether
  7. customgave a solid which
  8. customwas chromatographed on silica gel
  9. washElution with chloroform
  10. customgave a solid which
  11. customwas crystallised from ethyl acetate/petrol

Sources & evidence

ORD record
ord-405fb51472444c9bb0b6c1a65ea6df1b
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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