Sodium borohydride → HCID 19385048, compound

HRID 2399906Notes

Reaction equation

HRID 2399906 reaction equation
[BH4-].[Na+].[C:3]([O:6][CH:7]([C:20]1[CH:24](O)[O:23][C:22](=[O:26])[C:21]=1[CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:5])[CH3:4]>C1COCC1>[C:3]([O:6][CH:7]([C:20]1[CH:21]([CH3:27])[C:22](=[O:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15228017HCID 15228017, compound

Product 1

HCID 19385048HCID 19385048, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (25 mg, 0.67 mmol) was added to a solution of 4-(1-acetoxytridecyl)-3-methyl-5-hydroxy-2(5-H)-furanone (157 mg, 0.44 mmol) in anhydrous THF (20 mL) at room temperature under argon. After 2 hours aqueous HCL (1N) was added carefully until pH2 was reached and the resulting mixture was stirred an additional 1 hour. This mixture was extracted with ethyl acetate and the combined organic fractions were washed with 5% sodium bicarbonate 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. Fractions with Rf of about 0.45 on evaporation afforded the title compound.

Workup

  1. additionAfter 2 hours aqueous HCL (1N) was added carefully until pH2
  2. extractionThis mixture was extracted with ethyl acetate
  3. washthe combined organic fractions were washed with 5% sodium bicarbonate and brine
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil which
  7. customwas purified by flash chromatography on silica using 30% ethyl acetate/hexane
  8. customFractions with Rf of about 0.45 on evaporation

Sources & evidence

ORD record
ord-344c41a90d86481cac076716730797a8
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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