Hexane → HCID 178478637, compound

HRID 1983807Notes

Reaction equation

HRID 1983807 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:2]1.C([Li])CCC.CCCCCC.O1CCCC1.O1CCCC1.O1CCCC1.[Cl-:44].[Cl-].[Cl-].[Cr+3:47]>O1CCCC1>[Cl-:44].[Cl-:44].[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH2:10][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:1]=[C:2]1[Cr+2:47]

Participants

6

Reactant 4

HCID 8058HexaneHCID 121355622-[2-(1H-inden-3-yl)ethyl]pyridineHCID 25155609Tetrahydrofuran;trichlorochromiumHCID 178418339Butyllithium

Product 1

HCID 178478637HCID 178478637, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

A solution of 22.1 g (0.1 mol) of 2-[2-(1H-inden-3-yl)ethyl]pyridine in 470 ml of tetrahydrofuran was cooled to −100° C. 62.5 ml of a 15% strength n-butyllithium solution in hexane (0.1 mol) were slowly added dropwise. After the addition was complete, the reaction mixture was stirred for a further 50 minutes at −100° C. The mixture was subsequently allowed to warm to room temperature. After stirring for another 2 hours, the solution was cooled to −60° C. and 38 g (0.1 mol) of chromium trichloride tris(tetrahydrofuran) were added while stirring. The mixture was allowed to warm slowly to room temperature and was subsequently stirred for another 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 and washed with hot tetrahydrofuran. The solid was subsequently washed with diethyl ether and dried under reduced pressure. This gave 28.1 g of (1-(2-pyridylethyl)indenyl)chromium dichloride (82%).

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. stirringAfter stirring for another 2 hours
  4. temperaturethe solution was cooled to −60° C.
  5. stirringwhile stirring
  6. temperatureto warm slowly to room temperature
  7. stirringwas subsequently stirred for another 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 hot tetrahydrofuran
  13. washThe solid was subsequently washed with diethyl ether
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-ccbc22736284405a99dfa34d80ed4e2d
Source dataset
uspto-grants-2009_06
Patent number
US07541481B2

Reaction notes

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