Pyridine → HCID 178439351, compound

HRID 493404Notes

Reaction equation

HRID 493404 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[CH3:12][CH2:13][CH2:14]CCC.O1[CH2:22][CH2:21][CH2:20][CH2:19]1.O1CCC[CH2:24]1.[Cl-:28].[Cl-].[Cl-].[Cr+3:31]>O1CCCC1>[Cl-:28].[Cl-:28].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:9]([C:8]1[C:7]2[C:21](=[CH:22][CH:12]=[CH:13][CH:14]=2)[CH:20]([Cr+2:31])[CH:19]=1)([CH3:24])[CH3:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8058HexaneHCID 86602265Chromium trichloride bis(tetrahydrofuran)HCID 178418339Butyllithium

Product 1

HCID 178439351HCID 178439351, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

A solution of 0.54 g (0.0023 mol) of [2-1H-inden-3-yl)-1-methylethyl]pyridine in 20 ml of tetrahydrofuran was cooled to −100° C. 1.72 ml of a 15% strength n-butyllithium solution in hexane (0.0027 mol) were slowly added dropwise. After the addition was complete, the reaction mixture was stirred at −100° C. for a further 30 minutes. The mixture was subsequently allowed to warm to room temperature. After stirring for a further 1 hour, the solution was cooled to −60° C. and 1.1 g (0.0029 mol) of chromium trichloride bis(tetrahydrofuran) were added while stirring. The mixture was allowed to warm slowly to room temperature and was subsequently stirred for a further 10 hours at room temperature. The reaction mixture was then refluxed for 20 minutes and subsequently cooled to room temperature. The solid which had precipitated was filtered off, washed with diethyl ether and dried under reduced pressure. This gave 0.3 g of (3-(2-pyridyl-1-methylethyl)indenyl)chromium dichloride (37%).

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. stirringAfter stirring for a further 1 hour
  4. temperaturethe solution was cooled to −60° C.
  5. stirringwhile stirring
  6. temperatureto warm slowly to room temperature
  7. stirringwas subsequently stirred for a further 10 hours at room temperature
  8. temperatureThe reaction mixture was then refluxed for 20 minutes
  9. temperaturesubsequently cooled to room temperature
  10. customThe solid which had precipitated
  11. filtrationwas filtered off
  12. washwashed with diethyl ether
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-8070ee3b7f574d98be6744a89ac0bc44
Source dataset
uspto-grants-2009_05
Patent number
US07534847B2

Reaction notes

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