Acetic Acid → HCID 71476402, compound

HRID 527112Notes

Reaction equation

HRID 527112 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]3([OH:19])[C:11]4[C:16]([C:17](=[O:18])[C:8]3([OH:20])[C:7]=2[CH:21]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH3:2].[C:22]([OH:25])(=O)[CH3:23].N1C=CC=CC=1.C1C[O:35][CH2:34][CH2:33]1>>[C:34]([O:10][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:21][C:7]=1[C:8]1([O:20][C:22](=[O:25])[CH3:23])[C:9](=[O:19])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]1=[O:18])(=[O:35])[CH3:33]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71488533HCID 71488533, compound

Product 1

HCID 71476402HCID 71476402, compoundYield 27%

Procedure

8-Ethyl-4b,9b-dihydroxy-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (0.80 g, 2.70 mmol) was completely dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (0.57 ml, 5.66 mmol), pyridine (0.22 ml, 2.83 mmol), and 4-dimethyl aminopyridine (0.08 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 1:2) to afford the title compound (0.56 g, 27%).

Workup

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

Sources & evidence

ORD record
ord-2289cc88834b4ff08e7b427c007e3233
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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