Toluene → HCID 178448020, compound

HRID 1590801Notes

Reaction equation

HRID 1590801 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13](Br)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Li].C1(C)C=CC=CC=1.Br[C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH3:34])=[N:30][CH:31]=1>[Zn+2].[Br-].[Br-].C1COCC1>[CH2:33]([O:32][C:29]1[CH:28]=[CH:27][C:26]([C@H:13]2[CH2:14][CH2:15][C@H:10]([C@H:7]3[CH2:6][CH2:5][C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]3)[CH2:11][CH2:12]2)=[CH:31][N:30]=1)[CH3:34]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8172375-Bromo-2-ethoxypyridineHCID 3028194LithiumHCID 178448001HCID 178448001, compound

Product 1

HCID 178448020HCID 178448020, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.02 m of trans-4-(trans-4-propylcyclohexyl)-cyclohexylbromide, 0.04 m of lithium, 0.01 m of ZnBr2, 40 ml of toluene and 12 ml of THF are stirred at 0°-10° for 2 hours under ultrasonic. The 0.02 m of 5-bromo-2-ethoxy-pyridine and 0.5 g Pd (Ph3P)4 as the catalyst are added, and the mixture is stirred for further 4 hours at room temperature. Customary work-up yields 2-ethoxy-5-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-pyridine.

Sources & evidence

ORD record
ord-c781d56261e64926b917ec27bf424004
Source dataset
uspto-grants-1993_04
Patent number
US05204477

Reaction notes

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