Cesium carbonate → HCID 17962873, compound

HRID 2382302Notes

Reaction equation

HRID 2382302 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:31][CH:32]1[CH2:34][CH2:33]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:31][CH:32]3[CH2:34][CH2:33]3)=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH3:15])[CH2:6][C:5]1([CH3:23])[CH3:22])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 80013(Chloromethyl)cyclopropaneHCID 17962881HCID 17962881, compound

Product 1

HCID 17962873HCID 17962873, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-acetyl-6-hydroxy-4-phenyl-1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (20 mg), cesium carbonate (63 mg), tetrabutylammonium bromide (29 mg) and chloromethylcyclopropane (8.4 l) in acetonitrile (1 ml) was stirred at 50° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>6/4 (v/v) as eluent.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was chromatographed on silicagel in heptane/ethyl acetate=1/0=>6/4 (v/v) as eluent

Sources & evidence

ORD record
ord-9a22fcc4530e400f93e67a976b0cfbc9
Source dataset
uspto-grants-2012_09
Patent number
US08258293B2

Reaction notes

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