Potassium Hydroxide → HCID 86717342, compound

HRID 527136Notes

Reaction equation

HRID 527136 reaction equation
[OH:1][C:2]12[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=O)[C:6]1([OH:15])[C:5]1[CH:16]=[CH:17][C:18]([CH:20]([CH3:22])[CH3:21])=[CH:19][C:4]=1[O:3]2.O.NN.[OH-].[K+]>C(O)COCCO>[OH:15][C:6]1([C:5]2[CH:16]=[CH:17][C:18]([CH:20]([CH3:21])[CH3:22])=[CH:19][C:4]=2[OH:3])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 71488345HCID 71488345, compound

Product 1

HCID 86717342HCID 86717342, compoundYield 6,439.8%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4b,9b-dihydroxy-7-isopropyl-4bH-benzo[d]indeno[1,2-b]furan-10(9bH)-one (1.0 g, 3.3 mmol) in diethylene glycol (10 ml) were added with hydrazine hydrate (80%, 0.36 g, 9.6 mmol), followed by stirring at 150° C. for 15 min. The reaction mixture was added potassium hydroxide (360 mg, 6.4 mmol), and stirred at 165-170° C. for 1 hrs. The reaction mixture was extracted with ethylacetate, and purified using column chromatography (20% ethylacetate in hexane) to afford the title compound (60 g, 6.5%).

Workup

  1. stirringstirred at 165-170° C. for 1 hrs
  2. extractionThe reaction mixture was extracted with ethylacetate
  3. custompurified

Sources & evidence

ORD record
ord-38e1ea2ccbfc486ea7ae1417fdbaaaa2
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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