Water → HCID 24886486, compound

HRID 1912227Notes

Reaction equation

HRID 1912227 reaction equation
[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH:6]1[C:10](=[O:11])[CH2:9][CH2:8][CH:7]1[CH2:12][C:13]([OH:15])=[O:14].[BH4-].[Na+].O>C(O)C>[OH:11][CH:10]1[CH2:9][CH2:8][C@H:7]([CH2:12][C:13]([OH:15])=[O:14])[C@H:6]1[CH2:5]/[CH:4]=[CH:3]\[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 12304694HCID 12304694, compound

Product 1

HCID 24886486HCID 24886486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

In a 50 ml three-necked flask equipped with a condenser, a thermometer and a magnetic stirrer, 1 g (4.8 mmol) of (+/−)-jasmonic acid was dissolved in 15 ml of absolute ethanol. 430 mg (11.4 mmol) of sodium borohydride, NaBH4, were added. The mixture was stirred at 50° C. for 4 hours. When the reaction was finished, 5 ml of water were added slowly. The precipitate formed was filtered off. The filtrate was acidified to pH=5 with hydrochloric acid and then extracted with ethyl acetate (3×30 ml). The organic phase was dried over sodium sulphate, filtered on filter paper, and then concentrated. The colourless oil obtained was purified by chromatography on silica gel (eluent: dichloro-methane/methanol). The colourless oil obtained was dried under vacuum.

Workup

  1. customIn a 50 ml three-necked flask equipped with a condenser
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. filtrationon filter paper
  8. concentrationconcentrated
  9. customThe colourless oil obtained
  10. customwas purified by chromatography on silica gel (eluent: dichloro-methane/methanol)
  11. customThe colourless oil obtained
  12. customwas dried under vacuum

Sources & evidence

ORD record
ord-f669ae9d1558485c81fce4506bf9bec4
Source dataset
uspto-grants-2013_12
Patent number
US08609117B2

Reaction notes

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