Sodium borohydride → 2-(1-Hydroxyethyl)naphtho[2,3-b]furan-4,9-dione

HRID 1746923Notes

Reaction equation

HRID 1746923 reaction equation
[C:1]([C:4]1[O:8][C:7]2[C:9](=[O:18])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[BH4-].[Na+]>CN(C=O)C.O>[OH:3][CH:1]([C:4]1[O:8][C:7]2[C:9](=[O:18])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 103318442-Acetylfuro-1,4-naphthoquinone

Product 1

HCID 1500682-(1-Hydroxyethyl)naphtho[2,3-b]furan-4,9-dioneYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In a 250 ml beaker, 2 grams (8.3 mmoles) of 2-acetyl-naphtho[2,3-b]furan-4,9-dione (prepared in example 2 or 3) was dissolved in 40 ml of DMF with heating. To the solution with stirring, 1 gram (26.4 mmoles) of sodium borohydride in 10 ml of water was added. The mixture was stirred in open air for 30 minutes, then diluted by adding 250 ml of water. The resulting mixture was extracted with 100 ml of dichloromethane twice. The combined organic phase was washed with 200 ml of water, dried with anhydrous sodium sulfate, and evaporated to dryness. The residue was crystallized in ethyl acetate to yield 1.6 gram (6.6 mmoles) of pure product with overall yield 80%. Pure product was characterized by 1H NMR and mass spectrum. 1H NMR (in DMSO) δ 1.47 (d, J=7, 3H), 4.88 (m, 1H), 5.83 (d, J=5, 1H), 6.91 (s, 1H), 7.84-7.90 (m, 2H), 8.06-8.11 (m, 2H). Mass (M+H) is 243.

Workup

  1. temperaturewith heating
  2. stirringThe mixture was stirred in open air for 30 minutes
  3. additiondiluted
  4. extractionThe resulting mixture was extracted with 100 ml of dichloromethane twice
  5. washThe combined organic phase was washed with 200 ml of water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was crystallized in ethyl acetate

Sources & evidence

ORD record
ord-b5d6f9a7029242ab8d46cdcd5b270818
Source dataset
uspto-grants-2015_10
Patent number
US09150530B2

Reaction notes

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