Hexane → HCID 178478638, compound

HRID 1009686Notes

Reaction equation

HRID 1009686 reaction equation
[CH2:1]1C2C(=CC=CC=2)[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:2]1.C([Li])CCC.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].O1CCCC1.O1CCCC1.O1CCCC1.[Cl-:49].[Cl-].[Cl-].[Cr+3:52]>O1CCCC1>[Cl-:49].[Cl-:49].[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:16]([C:11]1[C:1]2[C:14](=[CH:15][CH:10]=[CH:3][CH:2]=2)[CH:13]([Cr+2:52])[CH:12]=1)[C:30]1[CH:29]=[CH:28][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 25155609Tetrahydrofuran;trichlorochromiumHCID 67326808HCID 67326808, compoundHCID 178418339Butyllithium

Product 1

HCID 178478638HCID 178478638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

A solution of 4.63 g (0.016 mol) of [2-(1H-inden-3-yl)(phenyl)methyl]pyridine in 60 ml of tetrahydrofuran was cooled to −100° C. 11 ml of a 15% strength n-butyllithium solution in hexane (0.016 mol) were slowly added dropwise. After the addition was complete, the reaction mixture was stirred at −100° C. for a further one hour. The mixture was subsequently allowed to warm to room temperature. After stirring for a further one hour, the solution was cooled to −60° C. and 6.15 g (0.016 mol) of chromium trichloride tris(tetrahydrofuran) was 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, washed with diethyl ether and dried under reduced pressure. This gave 4.4 g of (3-(2-pyridyl-1-phenylmethyl)indenyl)chromium dichloride (40%).

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. stirringAfter stirring for a further one hour
  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 diethyl ether
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-b0fd8e39d8a44df8b156fa60ec22dddd
Source dataset
uspto-grants-2011_07
Patent number
US07973114B2

Reaction notes

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