1-Penten-3-one → HCID 90034429, compound

HRID 1483147Notes

Reaction equation

HRID 1483147 reaction equation
[CH3:1][C@H:2]1[C@:9]2([O:14][C:13]3[C:15]([Cl:23])=[C:16]([O:21][CH3:22])[CH:17]=[C:18]([O:19][CH3:20])[C:12]=3[C:10]2=[O:11])[C:7](=[O:8])[CH2:6][C:4](=O)[CH2:3]1.C([O-])(=O)C.[NH4+:28].[CH:29]([C:31]([CH2:33]C)=O)=[CH2:30]>C(O)C>[Cl:23][C:15]1[C:13]2[O:14][C@:9]3([C@H:2]([CH3:1])[CH2:3][C:4]4[N:28]=[C:31]([CH3:33])[CH:29]=[CH:30][C:6]=4[C:7]3=[O:8])[C:10](=[O:11])[C:12]=2[C:18]([O:19][CH3:20])=[CH:17][C:16]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 153941-Penten-3-oneHCID 517165Ammonium AcetateHCID 71317160Griseofulvic acid

Product 1

HCID 90034429HCID 90034429, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL round-bottomed flask was charged with 1 g (2.9 mmol, 1 eq.) of griseofulvic acid, 0.34 g (4.4 mmol, 1.5 eq.) ammonium acetate and 347 μL (3.5 mmol, 1.2 eq.) of ethyl vinyl ketone in 10 mL ethanol. The mixture was left under agitation for 4 h at 80° C., cooled to ambient temperature then concentrated under reduced pressure. The residue was purified by chromatography on silica gel (CH2Cl2/AcOEt 98:2 to 80:20). A yellow solid (0.25 g) was obtained with a yield of 21%.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by chromatography on silica gel (CH2Cl2/AcOEt 98:2 to 80:20)

Sources & evidence

ORD record
ord-7864413bab1c4498b9dd21405a32262d
Source dataset
uspto-grants-2016_08
Patent number
US09416143B2

Reaction notes

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