Sodium borohydride → HCID 19385051, compound

HRID 2399908Notes

Reaction equation

HRID 2399908 reaction equation
[BH4-].[Na+].[OH:3][CH:4]([C:17]1[C:21](O)([CH3:22])[O:20][C:19](=[O:24])[CH:18]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>COCCOC>[OH:3][CH:4]([C:17]1[CH:21]([CH3:22])[O:20][C:19](=[O:24])[CH:18]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19385050HCID 19385050, compound

Product 1

HCID 19385051HCID 19385051, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

NaBH4 (210 mg, 5.54 mmol) was added in portions to a solution of 4-(1-hydroxytridecyl)-5-hydroxy-5-methyl-2-furanone (586 mg, 1.85 mmol) in anhydrous ethyle glycol dimethyl ether (60 mL) at 0° C. under argon. After stirring for 3 hours at 0° C. the reaction was quenched with HCl (6N) to pH2 and extracted with 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 as a mixture of diastereomers. Recrystallization from diethyl ether/hexane gave a single diastereomer.

Workup

  1. customwas quenched with HCl (6N) to pH2
  2. extractionextracted with ethyl acetate
  3. washThe combined organic fractions were washed with a saturated solution of aqueous sodium bicarbonate, H2O 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

Sources & evidence

ORD record
ord-f4f2b6750cef418485c5a24e513564c6
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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