Acetic Acid → HCID 71476274, compound

HRID 527107Notes

Reaction equation

HRID 527107 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3([OH:18])[C:15](=[O:16])[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:7]3([OH:17])[O:8][C:4]=2[CH:3]=1.[C:21]([OH:24])(=O)[CH3:22].N1C=CC=CC=1.C1C[O:34][CH2:33][CH2:32]1>>[C:33]([O:8][C:4]1[CH:3]=[C:2]([Cl:1])[CH:20]=[CH:19][C:5]=1[C:6]1([O:18][C:21](=[O:24])[CH3:22])[C:7](=[O:17])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]1=[O:16])(=[O:34])[CH3:32]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71652914HCID 71652914, compound

Product 1

HCID 71476274HCID 71476274, compoundYield 19%

Procedure

7-Chloro-4b,9b-dihydroxy-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (2.00 g, 6.9 mmol) was completely dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (1.41 ml, 13.8 mmol), pyridine (0.55 ml, 6.9 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=1:3) to afford the title compound (0.51 g, 19%).

Workup

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

Sources & evidence

ORD record
ord-89ad8ed2dbde424b95e269ddd797e3c6
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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