Hexane → HCID 70150555, compound

HRID 2303751Notes

Reaction equation

HRID 2303751 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.C([Li])CCC.CCCCCC.Cl[P:24]([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26].Cl[Sn:32]([CH2:41][CH2:42][CH2:43][CH3:44])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36]>CCOCC>[CH:25]([P:24]([C:5]1[CH:4]([Sn:32]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:33][CH2:34][CH2:35][CH3:36])[C:3]2[C:7]([CH:6]=1)=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=2[CH3:1])[CH:28]([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

7

Reactant 5

HCID 8058Hexane2×HCID 15096Tributyltin ChlorideHCID 814584,7-dimethyl-1H-indene2×HCID 538967ChlorodiisopropylphosphineHCID 178418339Butyllithium2×

Product 1

HCID 70150555HCID 70150555, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

100 ml of ether were placed in a round-bottomed flask containing 5.0 g (0.035 moles) of 4,7-dimethylindene (compound 21); the solution was cooled to −20° C. 14 ml of a 2.5 molar solution of butyllithium in hexane (0.035 moles) were added over 5 min to form a yellow solution. After removal of the cooling bath, the solution was heated to room temperature and subsequently stirred for 1 h. After cooling of the reaction mixture to −20° C., 5.3 g (0.035 moles) of chlorodiisopropylphosphine were added over 5 min to form a precipitate. The cooling bath was then removed and the reaction mixture was stirred for 1 h at room temperature. After cooling to −20° C., 14.0 ml of a 2.5 molar solution of butyllithium in hexane (0.035 moles) were added dropwise. When the addition was complete, the cooling bath was removed and the solution was heated slowly to room temperature and stirred for 1.5 h. After cooling of the suspension to 0° C., 11.4 g of chlorotributyltin (0.035 moles) were added dropwise. The suspension formed was heated to room temperature and stirred for 1.5 h. The ether was removed under vacuum, the crude product was dissolved in hexane again, the solution was filtered and the filtrate was concentrated under vacuum to leave 16 g (yield: 83%) of compound 22 in the form of a heavy yellow oil. 31P NMR (161.9 MHz, CD2Cl2): δ=−9 ppm.

Workup

  1. customto form a yellow solution
  2. customAfter removal of the cooling bath
  3. temperaturethe solution was heated to room temperature
  4. temperatureAfter cooling of the reaction mixture to −20° C.
  5. customto form a precipitate
  6. customThe cooling bath was then removed
  7. stirringthe reaction mixture was stirred for 1 h at room temperature
  8. temperatureAfter cooling to −20° C.
  9. additionWhen the addition
  10. customthe cooling bath was removed
  11. temperaturethe solution was heated slowly to room temperature
  12. stirringstirred for 1.5 h
  13. temperatureAfter cooling of the suspension to 0° C.
  14. customThe suspension formed
  15. temperaturewas heated to room temperature
  16. stirringstirred for 1.5 h
  17. customThe ether was removed under vacuum
  18. dissolutionthe crude product was dissolved in hexane again
  19. filtrationthe solution was filtered
  20. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-babcee2751da4f3f8879a38ef1bbf27a
Source dataset
uspto-grants-2002_08
Patent number
US06433112B1

Reaction notes

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