Acetic Acid → HCID 71476279, compound

HRID 527109Notes

Reaction equation

HRID 527109 reaction equation
[OH:1][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]=[CH:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:19][C:4]=1[O:3]2.[C:26]([OH:29])(=O)[CH3:27].N1C=CC=CC=1.C1C[O:39][CH2:38][CH2:37]1>>[C:38]([O:3][C:4]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][C:5]=1[C:6]1([O:15][C:26](=[O:29])[CH3:27])[C:2](=[O:1])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:14])(=[O:39])[CH3:37]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 86717338HCID 86717338, compound

Product 1

HCID 71476279HCID 71476279, compoundYield 11%

Procedure

4b,9b-Dihydroxy-7-phenyl-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (2.00 g, 6.0 mmol) was dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (1.24 ml, 12.1 mmol), pyridine (0.48 ml, 6.0 mmol), and 4-dimethyl aminopyridine (0.2 g), and stirred at room temperature for 12 hrs. After the reaction mixture was extracted with dichloromethane, the organic layer was concentrated and purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (0.41 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-026083fe257b4c7aa00ce6cec09c108f
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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