Hexane → HCID 178478636, compound

HRID 1009681Notes

Reaction equation

HRID 1009681 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:2]1.C1(=C/C2C=CC=CN=2)/CCC2C/1=CC=CC=2.C([Li])CCC.CCCCCC.O1CCCC1.O1CCCC1.O1CCCC1.[Cl-:59].[Cl-].[Cl-].[Cr+3:62]>O1CCCC1>[Cl-:59].[Cl-:59].[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[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+2:62]

Participants

7

Reactant 5

HCID 8058HexaneHCID 5474041HCID 5474041, compoundHCID 121245902-(1H-inden-3-ylmethyl)pyridineHCID 25155609Tetrahydrofuran;trichlorochromiumHCID 178418339Butyllithium

Product 1

HCID 178478636HCID 178478636, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

A solution of 52.7 g of the above mixture of 2-(1H-inden-3-ylmethyl)pyridine and 2-[(E)-2,3-dihydro-1H-inden-1-ylidenemethyl]pyridine in a molar ratio of 10:9 in 550 ml of tetrahydrofuran was cooled to −100° C. 80.5 ml of a 15% strength n-butyllithium solution in hexane (0.1288 mol) were then slowly added dropwise. After the addition was complete, the reaction mixture was stirred at −100° C. for a further 45 minutes. The mixture was subsequently allowed to warm to room temperature. After stirring for a further 2 hours, the solution was cooled to 60° C. and 49 g (0.1288 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 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 and washed with hot tetrahydrofuran. The solid was subsequently washed with diethyl ether and dried under reduced pressure. This gave 24.9 g of (1-(2-pyridylmethyl)indenyl)chromium dichloride (59%).

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. stirringAfter stirring for a further 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 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 hot tetrahydrofuran
  13. washThe solid was subsequently washed with diethyl ether
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-ac90dc4b4ee94fa2adb1b4288b83bc59
Source dataset
uspto-grants-2011_07
Patent number
US07973114B2

Reaction notes

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