Acetic Acid → HCID 71476404, compound

HRID 527115Notes

Reaction equation

[CH:1]([C:5]1[CH:23]=[CH:22][C:8]2[C:9]3([OH:21])[C:18](=[O:19])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:10]3([OH:20])[O:11][C:7]=2[CH:6]=1)([CH2:3]C)[CH3:2].[C:24]([OH:27])(=O)[CH3:25].N1C=CC=C[CH:29]=1.C1C[O:37][CH2:36][CH2:35]1>>[C:36]([O:11][C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:29])[CH3:3])[CH:23]=[CH:22][C:8]=1[C:9]1([O:21][C:24](=[O:27])[CH3:25])[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]1=[O:20])(=[O:37])[CH3:35]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 1049Pyridine

HCID 8028Tetrahydrofuran

HCID 90097613HCID 90097613, compound

Product 1

HCID 71476404HCID 71476404, compoundYield 42%

Procedure

7-sec-Butyl-4b,9b-dihydroxy-4bH-benzo[d]indeno[1,2-b]-furan-10(9bH)-one (0.52 g, 1.67 mmol) was completely dissolved in anhydrous THF (20 ml). This solution was added with anhydrous acetic acid (0.34 g, 3.3 mmol), pyridine (0.13 g, 1.6 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 (0.53 g, 42%).

Workup

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

Sources & evidence

ORD record: ord-03daa3bd2bc940ff8c06b21d28748a70
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346749B2

Reaction notes

Loading…