Acetic Acid → HCID 71476531, compound

HRID 527116Notes

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

Participants

Reactant 4

HCID 176Acetic Acid

HCID 1049Pyridine

HCID 8028Tetrahydrofuran

HCID 71488539HCID 71488539, compound

Product 1

HCID 71476531HCID 71476531, compoundYield 38%

Procedure

4b,9b-Dihydroxy-8-tert-pentyl-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (0.80 g, 2.46 mmol) was dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (0.50 g, 4.93 mmol), pyridine (0.19 ml, 2.46 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=1:3) to afford the title compound (0.71 g, 38%).

Workup

extractionAfter the reaction mixture was extracted with dichloromethane
concentrationthe organic layer was concentrated
custompurified

Sources & evidence

ORD record: ord-edfca449af5e4171b1842420af493af2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346749B2

Reaction notes

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