Acetic Acid → HCID 71476148, compound

HRID 527106Notes

Reaction equation

HRID 527106 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]=[C:17]([CH3:21])[C:18]([CH3:20])=[CH:19][C:4]=1[O:3]2.[C:22]([OH:25])(=O)[CH3:23].N1C=CC=CC=1.C1C[O:35][CH2:34][CH2:33]1>>[C:34]([O:3][C:4]1[CH:19]=[C:18]([CH3:20])[C:17]([CH3:21])=[CH:16][C:5]=1[C:6]1([O:15][C:22](=[O:25])[CH3:23])[C:7](=[O:14])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]1=[O:1])(=[O:35])[CH3:33]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71488293HCID 71488293, compound

Product 1

HCID 71476148HCID 71476148, compoundYield 42%

Procedure

4b,9b-Dihydroxy-7,8-dimethyl-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (1.00 g, 3.5 mmol) was dissolved in anhydrous THF (50 ml). This solution was added with anhydrous acetic acid (0.67 ml, 7.1 mmol), pyridine (0.30 ml, 3.5 mmol), and 4-dimethyl aminopyridine (0.1 g), and stirred at room temperature for 3 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 (0.55 g, 42%).

Workup

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

Sources & evidence

ORD record
ord-6294db335f17487e8c3bacdf88295ee4
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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