Sodium borohydride → 5-Hydroxy-2-(1-Hydroxyethyl)Naphtho(2,3-B)Furan-4,9-Dione

HRID 604944Notes

Reaction equation

HRID 604944 reaction equation
[C:1]([C:4]1[O:8][C:7]2[C:9](=[O:19])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[C:14]([OH:18])[CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[BH4-].[Na+]>C(Cl)(Cl)Cl.C(O)C>[OH:3][CH:1]([C:4]1[O:8][C:7]2[C:9](=[O:19])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[C:14]([OH:18])[CH:13]=[CH:12][CH:11]=3)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 100152592-Acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione

Product 1

HCID 1477195-Hydroxy-2-(1-Hydroxyethyl)Naphtho(2,3-B)Furan-4,9-DioneYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione (694 mg, 2.73 mmol) obtained in Example 5 in chloroform (100 mL) and ethanol (25 mL) is added sodium borohydride (515 mg, 13.7 mmol) at 0° C. The mixture is stirred for 30 minutes, and then the reaction is quenched by adding 10% hydrochloric acid to the mixture. The aqueous layer is extracted with chloroform twice, and the extract is continuously washed with water and brine. The mixture is evaporated in vacuo and purified by silica gel column chromatography (eluent: chloroform) to give 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione (516 mg, 74%) as a racemic mixture of a yellow crystal.

Workup

  1. customthe reaction is quenched
  2. additionby adding 10% hydrochloric acid to the mixture
  3. extractionThe aqueous layer is extracted with chloroform twice
  4. washthe extract is continuously washed with water and brine
  5. customThe mixture is evaporated in vacuo
  6. custompurified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-5e51723fa8224d4083afab720bfc0df6
Source dataset
uspto-grants-2011_03
Patent number
US07910752B2

Reaction notes

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