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

HRID 495080Notes

Reaction equation

HRID 495080 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].C(Cl)Cl.C(N(CC)CC)C.C(O)=O>O.Cl>[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

6

Reactant 3

HCID 6344DichloromethaneHCID 100152592-Acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dioneHCID 11084032Triethylammonium formate

Product 1

HCID 1477195-Hydroxy-2-(1-Hydroxyethyl)Naphtho(2,3-B)Furan-4,9-DioneYield 89.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

Into a flask were added 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione (128 mg, 0.5 mmol), Ru[(S,S)-Tsdpen](p-cymene) (15 mg, 0.025 mmol, 5 mol %), methylene chloride (5 mL) and formic acid-triethylamine mixture (5:2, 1.3 ml). The resulting suspension mixture was stirred at room temperature for 24 hours, and then diluted with water and 10% aqueous hydrochloric acid solution. The aqueous layer was extracted with chloroform twice, and the extract was washed with water and a saturated aqueous sodium chloride solution sequentially, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to give 2-(1-hydroxyethyl)-5-hydroxynaphtho[2,3-b]furan-4,9-dione (NQ801) (115 mg, 89%, 96% ee) as a yellow crystal.

Workup

  1. extractionThe aqueous layer was extracted with chloroform twice
  2. washthe extract was washed with water
  3. customa saturated aqueous sodium chloride solution sequentially, and evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-c09cf4d14e08418c9c93d1be6a7da6ee
Source dataset
uspto-grants-2009_05
Patent number
US07538234B2

Reaction notes

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