Toluene → HCID 178444261, compound

HRID 274182Notes

Reaction equation

HRID 274182 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15](OB(O)O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25](Cl)[N:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1(C)C=CC=CC=1.CCCCCC.O.CCCCCC>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[N:24]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 169892,6-DichloropyridineHCID 178444349HCID 178444349, compound

Product 1

HCID 178444261HCID 178444261, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 21889329Toluene hexaneSolvent

Procedure

A mixture of 0.23 mol of 4-(trans-4-pentylcyclohexyl)phenylboric acid, 0.23 mol of 2,6-dichloropyridine, 5 mmol of TPP, 230 ml of a 2 molar sodium carbonate solution and 400 ml of toluene are heated at the boil for 1 hour. The reaction mixture is cooled, and 200 ml of hexane and 200 ml of water are added. The organic phase is separated off, the solvent is removed by evaporation, and the pure product is obtained by chromatography on silica gel using toluene/hexane 3:1 as the eluent.

Workup

  1. temperatureare heated at the boil for 1 hour
  2. temperatureThe reaction mixture is cooled
  3. customThe organic phase is separated off
  4. customthe solvent is removed by evaporation
  5. customthe pure product is obtained by chromatography on silica gel

Sources & evidence

ORD record
ord-af4300a24846456a980c26337d846e8b
Source dataset
uspto-grants-1995_02
Patent number
US05389291

Reaction notes

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