Acetic Acid → HCID 71476277, compound

HRID 527108Notes

Reaction equation

HRID 527108 reaction equation
[CH2:1]([C:3]1[CH:21]=[CH:20][C:6]2[C:7]3([OH:19])[C:16](=[O:17])[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:8]3([OH:18])[O:9][C:5]=2[CH:4]=1)[CH3:2].[C:22]([OH:25])(=O)[CH3:23].N1C=CC=CC=1.C1C[O:35][CH2:34][CH2:33]1>>[C:34]([O:9][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[CH:21]=[CH:20][C:6]=1[C:7]1([O:19][C:22](=[O:25])[CH3:23])[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8]1=[O:18])(=[O:35])[CH3:33]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71488344HCID 71488344, compound

Product 1

HCID 71476277HCID 71476277, compoundYield 88%

Procedure

7-Ethyl-4b,9b-dihydroxy-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (2.00 g, 7.0 mmol) was completely dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (1.44 ml, 14.1 mmol), pyridine (0.56 ml, 7.0 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 (2.28 g, 88%).

Workup

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

Sources & evidence

ORD record
ord-441fc6c8bf0b4ecc9ffd701c0e67dcc1
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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