Tetrahydrofuran → 2-(1,3-Dioxo-2-(propionyloxy)-2,3-dihydro-1H-inden-2-yl)-5-isopropylphenyl propionate

HRID 527118Notes

Reaction equation

HRID 527118 reaction equation
[OH:1][C:2]1([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][C:14]=2[OH:22])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[C:23](Cl)(=[O:26])[CH2:24][CH3:25].C(N(CC)CC)C.[CH2:35]1C[O:38][CH2:37][CH2:36]1>>[C:23]([O:22][C:14]1[CH:15]=[C:16]([CH:19]([CH3:20])[CH3:21])[CH:17]=[CH:18][C:13]=1[C:2]1([O:1][C:37](=[O:38])[CH2:36][CH3:35])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12])(=[O:26])[CH2:24][CH3:25]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 30544341H-Indene-1,3(2H)-dione, 2-hydroxy-2-(2-hydroxy-4-(1-methylethyl)phenyl)-

Product 1

HCID 714765352-(1,3-Dioxo-2-(propionyloxy)-2,3-dihydro-1H-inden-2-yl)-5-isopropylphenyl propionateYield 17%

Procedure

2-hydroxy-2-(2-hydroxy-4-isopropyl-phenyl)-indan-1,3-dione (1.00 g, 3.37 mmol) was completely dissolved in anhydrous THF (20 ml). This solution was added with propionyl chloride (0.62 g, 6.74 mmol), and triethylamine (0.41 g, 4.04 mmol), followed by heating 12 hrs under reflux. After the reaction mixture was concentrated, extracted with dichloromethane, and the organic layer was concentrated and purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (White, 0.23 g, 17%).

Workup

  1. temperatureby heating 12 hrs
  2. temperatureunder reflux
  3. concentrationAfter the reaction mixture was concentrated
  4. extractionextracted with dichloromethane
  5. concentrationthe organic layer was concentrated
  6. custompurified

Sources & evidence

ORD record
ord-b51e8fcbe0c645ea8dd6864228b308ab
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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