Methanol → HCID 3275413, compound

HRID 863606Notes

Reaction equation

HRID 863606 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12](O)=[O:13])[C:6]=2[C:15]=1[CH3:16].B.CSC.CO>O1CCCC1>[OH:1][C:2]1[C:3]([CH3:18])=[C:4]([CH3:17])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([CH2:12][OH:13])[C:6]=2[C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 10131175HCID 10131175, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 3275413HCID 3275413, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 58.82 g (0,235 mol) of 2,3-dihydro-5-hydroxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid (see Example 1) in 500 ml of dry tetrahydrofuran is added dropwise over 30 minutes 50 ml of 10M borane-methyl sulfide and the resulting mixture is stirred at reflux temperature for 7 hours. After cooling, 120 ml of methanol is added carefully and the resulting solution is evaporated to dryness. The residue is taken up in ethyl acetate and the solution is washed with 2N hydrochloric acid, water, a sodium bicarbonate solution, and brine, and is dried over anhydrous sodium sulfate. Filtration and evaporation of solvent gives an oil that crystallizes from ethyl acetate/heptane to give 37.85 g of the title compound, m.p. 89°-90° C. Elemental analysis, IR, UV, and 1H-NMR spectra confirm the structure. A second crop of 12.60 g is obtained, raising the yield to 91%.

Workup

  1. temperatureat reflux temperature for 7 hours
  2. temperatureAfter cooling
  3. customthe resulting solution is evaporated to dryness
  4. washthe solution is washed with 2N hydrochloric acid, water
  5. dry with materiala sodium bicarbonate solution, and brine, and is dried over anhydrous sodium sulfate
  6. filtrationFiltration and evaporation of solvent
  7. customgives an oil
  8. customthat crystallizes from ethyl acetate/heptane

Sources & evidence

ORD record
ord-92a6e748fc94427785998b364b017a33
Source dataset
uspto-grants-1998_02
Patent number
US05721233

Reaction notes

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