Acetic Acid → HCID 71476679, compound

HRID 527122Notes

Reaction equation

HRID 527122 reaction equation
[OH:1][C:2]12[C:13]3[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]1([OH:17])[C:5]1[CH:18]=[CH:19][C:20]([CH:22]([CH3:24])[CH3:23])=[CH:21][C:4]=1[O:3]2.[C:25]([OH:28])(=O)[CH3:26].N1C=CC=CC=1.C1C[O:38][CH2:37][CH2:36]1>CN(C1C=CN=CC=1)C>[C:37]([O:17][C:6]1([C:5]2[CH:18]=[CH:19][C:20]([CH:22]([CH3:24])[CH3:23])=[CH:21][C:4]=2[O:3][C:25](=[O:28])[CH3:26])[C:7](=[O:16])[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[C:2]1=[O:1])(=[O:38])[CH3:36]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71487812HCID 71487812, compound

Product 1

HCID 71476679HCID 71476679, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4b, 9b-dihydroxy-7-isopropyl-2-methoxy-4bH-benzo[d]indeno[1,2-b]furan-10(9bH)-one (0.30 g, 0.91 mmol) was completely dissolved in anhydrous THF (10 ml). This solution was added with anhydrous acetic acid (0.18 g, 1.82 mmol), pyridine (0.07 g, 0.91 mmol) and DMAP (0.03 g), and stirred at room temperature. The reaction mixture was concentrated, and extracted with ethylacetate, and the concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:3) to afford the title compound (0.19 g, 51%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethylacetate
  3. customthe concentrated organic layer was purified

Sources & evidence

ORD record
ord-624c7095e7fa452aacd30611a5fe2892
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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