Acetic Acid → HCID 71476280, compound

HRID 527110Notes

Reaction equation

HRID 527110 reaction equation
O[C:2]12[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[C:6]1([OH:15])[C:5]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:4]=1[O:3]2.[C:23]([OH:26])(=[O:25])[CH3:24].N1C=CC=CC=1.C1C[O:36][CH2:35][CH2:34]1>>[C:23]([O:26][C:4]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:5]=1[C:6]1([O:15][C:35](=[O:36])[CH3:34])[C:7](=[O:14])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]1=[O:3])(=[O:25])[CH3:24]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71488399HCID 71488399, compound

Product 1

HCID 71476280HCID 71476280, compoundYield 11%

Procedure

4b,9b-Dihydroxy-8-nitro-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (0.80 g, 2.6 mmol) was dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (0.54 ml, 5.3 mmol), pyridine (0.21 ml, 2.6 mmol), and 4-dimethyl aminopyridine (0.08 g), and stirred at room temperature for 30 hrs. After the reaction mixture was extracted with dichloromethane, the organic layer was concentrated and purified using column chromatography (ethylacetate:hexane=1:2 to 1:1) to afford the title compound (0.44 g, 11%).

Workup

  1. extractionAfter the reaction mixture was extracted with dichloromethane
  2. concentrationthe organic layer was concentrated
  3. custompurified

Sources & evidence

ORD record
ord-ae28aa16ad8e48bea6377a38c1474353
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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