Acetic Acid → HCID 71476401, compound

HRID 527111Notes

Reaction equation

HRID 527111 reaction equation
[OH:1][C:2]12[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[C:6]1([OH:15])[C:5]1[CH:16]=[C:17]([CH2:20][CH2:21][CH3:22])[CH:18]=[CH:19][C:4]=1[O:3]2.[C:23]([OH:26])(=O)[CH3:24].N1C=CC=CC=1.C1C[O:36][CH2:35][CH2:34]1>>[C:35]([O:3][C:4]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][C:5]=1[C:6]1([O:15][C:23](=[O:26])[CH3:24])[C:7](=[O:14])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]1=[O:1])(=[O:36])[CH3:34]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 8028TetrahydrofuranHCID 71488472HCID 71488472, compound

Product 1

HCID 71476401HCID 71476401, compoundYield 56%

Procedure

4b,9b-Dihydroxy-8-propyl-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (0.80 g, 2.70 mmol) was dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (0.55 ml, 5.40 mmol), pyridine (0.21 ml, 2.7 mmol), and 4-dimethyl aminopyridine (0.08 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 (0.85 g, 56%).

Workup

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

Sources & evidence

ORD record
ord-49b361cde1eb413ba429ccbced52642d
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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