Acetone → HCID 66702641, compound

HRID 424452Notes

Reaction equation

HRID 424452 reaction equation
CC(C)=O.C(=O)([O-])[O-].[K+].[K+].[CH2:11](Br)/[CH:12]=[C:13](/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])\[CH3:14].[OH:22][C:23]1[CH:33]=[CH:32][C:26]2[N:27]=[C:28]([C:30]#[N:31])[S:29][C:25]=2[CH:24]=1>CCCCCCC.C(OCC)(=O)C>[CH2:11]([O:22][C:23]1[CH:33]=[CH:32][C:26]2[N:27]=[C:28]([C:30]#[N:31])[S:29][C:25]=2[CH:24]=1)/[CH:12]=[C:13](/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])\[CH3:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-HCID 98819122-Cyano-6-hydroxybenzothiazole

Product 1

HCID 66702641HCID 66702641, compoundYield 120%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

To a dry 25-ml round-bottomed flask containing acetone (5 mL), anhydrous potassium carbonate (1.2 g, 8.4 mmole), and geranyl bromide (1.5 mL, 7.3 mmole) was added 6-hydroxy-2-cyanobenzothiazole (1 g, 5.6 mmole). The mixture was refluxed under argon with stirring. Reaction progress was monitored by TLC analysis, developing with 2:1 heptane-ethyl acetate. After 20 h, the potassium carbonate was filtered from the cooled reaction mixture. The solution was concentrated in vacuo to yield 2.1 g of solid. The solid was further purified by flash chromatography using a mixture of 9:1 heptane-ethyl acetate. Appropriate fractions were pooled and evaporated to yield 0.84 g of solid. The structure was confirmed by 1H NMR analysis in DMSO-d6.

Workup

  1. temperatureThe mixture was refluxed under argon
  2. customReaction progress
  3. filtrationthe potassium carbonate was filtered from the cooled reaction mixture
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2bca2d632ccb4d79af3fbe0931ecdfe9
Source dataset
uspto-grants-2012_01
Patent number
US08106052B2

Reaction notes

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