Hydrochloric Acid → 3,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone

HRID 612543Notes

Reaction equation

HRID 612543 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[O:11][CH:12]([CH2:15][CH2:16][OH:17])[C:13]=1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[O:11][CH:12]([CH2:15][CH2:16][OH:17])[C:13]=1[O:14][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 547235963-benzyloxy-4-hydroxy-5-(2-hydroxyethyl)-2(5H)-furanone

Product 1

HCID 211841063,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanoneYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.25 g (5 mmol) of 3-benzyloxy-4-hydroxy-5-(2-hydroxyethyl)-2(5H)-furanone, 15 mL of THF, 871 μL (5.0 mmol) of diisopropylethylamine and 631 μL (5.2 mmol) of benzyl bromide were combined under argon. The reaction mixture was warmed to reflux for 5 hours, and upon cooling, a suspension formed which was poured into 50 mL of 5% aqueous HCl solution and extracted with 100 mL of ether. The ether fraction was separated and sequentially washed with 30 mL of 5% aqueous HCl, 30 mL of H2O, 30 mL of saturated NaHCO3 solution, 30 mL of H2O, 30 mL of brine, dried (MgSO4) and concentrated to a colorless oil. Purification over silica gel using EtOAc/hexanes (2/3) provided 3,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone as a faint pink colored oil (1.0 g, 60% yield).

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 5 hours
  3. temperatureupon cooling
  4. customa suspension formed which
  5. extractionextracted with 100 mL of ether
  6. customThe ether fraction was separated
  7. washsequentially washed with 30 mL of 5% aqueous HCl, 30 mL of H2O, 30 mL of saturated NaHCO3 solution, 30 mL of H2O, 30 mL of brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated to a colorless oil
  10. customPurification over silica gel

Sources & evidence

ORD record
ord-9f0df7c866a1464faa84fe48a9066bff
Source dataset
uspto-grants-1999_12
Patent number
US06005000

Reaction notes

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