Sodium borohydride → HCID 53819009, compound

HRID 2351956Notes

Reaction equation

HRID 2351956 reaction equation
C[O:2][CH:3]1[C:7]([CH2:8][CH2:9][CH:10]=[C:11]([CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH:12]=[O:13])=[CH:6][C:5](=[O:25])[O:4]1.[BH4-].[Na+]>CO>[OH:2][CH:3]1[O:4][C:5](=[O:25])[CH:6]=[C:7]1[CH2:8][CH2:9][CH:10]=[C:11]([CH2:12][OH:13])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:24])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54362927HCID 54362927, compound

Product 1

HCID 53819009HCID 53819009, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A solution of 100 mg of 2-[3-(2,5-dihydro-2-methoxy-5-oxo-3-furanyl)propylidene]-6,10-dimethyl-5,9-undecadienal (Example 15G) and 10.9 mg of sodium borohydride in 30 ml of dry methanol under an argon atmosphere was stirred for four hours at room temperature followed by four hours of stirring at 35° C. The reaction was quenched by the slow addition of water and the mixture was extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in 3 ml of tetrahydrofuran and 0.34 ml of 0.1N sodium hydroxide at room temperature and under argon. The solution was brought to reflux for two hours, cooled, and adjusted to pH 4 with the slow addition of 0.1N hydrochloric acid. Extraction with ether provided an organic solution which was washed with 0.01N hydrochloric acid and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The resulting oil was purified by medium pressure liquid chromatography over silica gel eluting with 1:2 hexane/ethyl acetate to afford 56.8 mg of the title product as an oil. Proton NMR, 13C NMR, and mass spectra were consistent with the desired structure.

Workup

  1. customThe reaction was quenched by the slow addition of water
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue was dissolved in 3 ml of tetrahydrofuran
  7. customat room temperature
  8. temperatureto reflux for two hours
  9. temperaturecooled
  10. additionadjusted to pH 4 with the slow addition of 0.1N hydrochloric acid
  11. extractionExtraction with ether
  12. customprovided an organic solution which
  13. washwas washed with 0.01N hydrochloric acid
  14. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  15. concentrationconcentrated in vacuo
  16. customThe resulting oil was purified by medium pressure liquid chromatography over silica gel eluting with 1:2 hexane/ethyl acetate

Sources & evidence

ORD record
ord-6f5a2feba24548ec9d9f205ce24d3317
Source dataset
uspto-grants-1989_10
Patent number
US04874782

Reaction notes

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