Acetic Acid → HCID 71476403, compound

HRID 527113Notes

Reaction equation

HRID 527113 reaction equation
[CH: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)([CH2:3][CH3:4])[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]([CH:1]([CH2:3][CH3:4])[CH3:2])=[CH:23][C:9]=1[C:10]1([O:22][C:24](=[O:27])[CH3:25])[C:11](=[O:21])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]1=[O:20])(=[O:37])[CH3:35]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71488534HCID 71488534, compound

Product 1

HCID 71476403HCID 71476403, compoundYield 48%

Procedure

8-sec-Butyl-4b,9b-dihydroxy-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (0.58 g, 1.8 mmol) was completely dissolved in anhydrous THF (10 ml). This solution was added with anhydrous acetic acid (0.39 ml, 3.7 mmol), pyridine (0.15 ml, 1.8 mmol), and 4-dimethyl aminopyridine (0.06 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 (0.70 g, 48%).

Workup

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

Sources & evidence

ORD record
ord-e3068511612c49338c2dfb4183f380e2
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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