Hydrochloric Acid → HCID 15295494, compound

HRID 2399911Notes

Reaction equation

HRID 2399911 reaction equation
[BH4-].[Na+].[OH:3][CH2:4][C:5]1[C:9](O)([CH3:10])[O:8][C:7](=[O:12])[C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>COCCOC>[OH:3][CH2:4][C:5]1[CH:9]([CH3:10])[O:8][C:7](=[O:12])[C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15295493HCID 15295493, compound2×

Product 1

HCID 15295494HCID 15295494, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To NaBH4 (147 mg, 3.88 mmol) suspended in anhydrous ethylene glycol dimethyl ether (20 mL) at 0° C. under argon was added 4-hydroxymethyl-5-hydroxy-5-methyl-3-phenyl-2-furanone (Compound 6) in ethylene glycol dimethyl ether (20 mL) dropwise. After stirring for 3 hours the solution was acidified to pH2 with 6N HCl, warmed to ambient temperature and stirred an additional 1 hour. The solution was concentrated to 10 mL volume and the organics were extracted into ethyl acetate. The combined organic fractions were washed with a saturated solution of aqueous sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 30% ethyl acetate/hexane to give the title compound.

Workup

  1. stirringstirred an additional 1 hour
  2. concentrationThe solution was concentrated to 10 mL volume
  3. extractionthe organics were extracted into ethyl acetate
  4. washThe combined organic fractions were washed with a saturated solution of aqueous sodium bicarbonate, H2O and brine
  5. customEvaporation of the
  6. dry with materialdried (magnesium sulfate)
  7. customextracts gave an oil which
  8. customwas purified by flash chromatography on silica using 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4d20a55cad2d4b21a273dda2889dab44
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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