Acetic Acid → HCID 90097543, compound

HRID 527114Notes

Reaction equation

HRID 527114 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]3([OH:21])[C:13]4[C:18]([C:19](=[O:20])[C:10]3([OH:22])[C:9]=2[CH:23]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4)([CH3:4])([CH3:3])[CH3:2].[C:24]([OH:27])(=O)[CH3:25].N1C=CC=CC=1.C1C[O:37][CH2:36][CH2:35]1>>[C:36]([O:12][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:23][C:9]=1[C:10]1([O:22][C:24](=[O:27])[CH3:25])[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]1=[O:21])(=[O:37])[CH3:35]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71488535HCID 71488535, compound

Product 1

HCID 90097543HCID 90097543, compoundYield 36%

Procedure

8-tert-Butyl-4b,9b-dihydroxy-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (0.50 g, 1.6 mmol) was completely dissolved in anhydrous THF (10 ml). This solution was added with anhydrous acetic acid (0.32 ml, 3.7 mmol), pyridine (0.13 ml, 1.8 mmol), and 4-dimethyl aminopyridine (0.05 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 (0.44 g, 36%).

Workup

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

Sources & evidence

ORD record
ord-85dbb0cea7814d17872e0c414109ad6f
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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