Hexane → HCID 178442385, compound

HRID 1009689Notes

Reaction equation

HRID 1009689 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)([CH3:15])[CH2:11][CH2:12][CH:13]=[CH2:14])=[CH:2]1.C([Li])CCC.CCCCCC.O1CCCC1.O1CCCC1.O1CCCC1.[Cl-:48].[Cl-].[Cl-].[Cr+3:51]>O1CCCC1>[Cl-:48].[Cl-:48].[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:1]([Cr+2:51])[CH:2]=1)([CH3:15])[CH2:11][CH2:12][CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 8058HexaneHCID 25155609Tetrahydrofuran;trichlorochromiumHCID 67326902HCID 67326902, compoundHCID 178418339Butyllithium

Product 1

HCID 178442385HCID 178442385, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-100 °C

Procedure

A solution of 4.81 g (0.01747 mol) of 2-[1-(1H-inden-3-yl)-1-methyl-4-pentenyl]pyridine in 60 ml of tetrahydrofuran was cooled to −100° C. 11.5 ml of a 15% strength n-butyllithium solution in hexane (0.01834 mol) were slowly added dropwise. After the addition was complete, the reaction mixture was stirred at −100° C. for a further 1 hour. The mixture was subsequently allowed to warm to room temperature. After stirring for a further 2 hour, the solution was cooled to −60° C. and 7.07 g (0.0189 mol) of chromium trichloride tris(tetrahydrofuran) were added while stirring. The mixture was allowed to warm slowly to room temperature and was subsequently stirred at room temperature for a further 10 hours. The solid which had precipitated was filtered off, washed with diethyl ether and dried under reduced pressure. Recrystallization from a mixture of dichloromethane and diethyle ether gave 2.5 g of (3-(2-pyridyl-1-methyl-4-pentenyl)indenyl)chromium dichloride (36%).

Workup

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

Sources & evidence

ORD record
ord-4f0a3a94ef554520aa2037ff88f176f5
Source dataset
uspto-grants-2011_07
Patent number
US07973114B2

Reaction notes

Loading…