Indene → HCID 70150899, compound

HRID 1274377Notes

Reaction equation

HRID 1274377 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([Li])CCC.[C:15]1([P:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)Cl)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:29]([Sn:33](Cl)([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH3:32]>C(OCC)C.CCCCCC>[CH2:38]([Sn:33]([C:2]1[CH:3]([P:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]2[C:9]([CH:1]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:39][CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 7219IndeneHCID 15096Tributyltin ChlorideHCID 66180ChlorodiphenylphosphineHCID 178418339Butyllithium2×

Product 1

HCID 70150899HCID 70150899, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

10 g (0.086 mol) of indene were introduced into a round-bottomed flask, diluted with 200 ml of diethyl ether and cooled to -20° C. 36 ml of a 2.36 molar solution of butyl-lithium (0.085 mol) in n-hexane were added to this solution, the solution immediately assuming a yellow color. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature and was stirred for a further hour. Thereafter, the reaction mixture was cooled again to 0° C. and 19 g (15.9 ml, 0.086 mol) of diphenylchlorophosphine were added, a precipitate being formed. The cooling bath was removed again and the solution was allowed to warm to room temperature while being subsequently stirred for a further hour. The solution was then cooled again to -20° C. and 36 ml (0.085 mol) of butyl-lithium in n-hexane were added dropwise. When the addition had ended, the cooling bath was removed again and the temperature rose to room temperature; the solution was subsequently stirred for a further 1.5 hours. The suspension was then cooled again to 0° C. and 28 g (0.086 mol) of tributyltin chloride were added dropwise. The resulting suspension was warmed to room temperature and stirred for a further 1.5 hours and subsequently filtered through a frit, and the solvent was removed in vacuo. 46.9 g of the compound 8 (92% of the theoretical yield) remained as a heavy yellow oil.

Workup

  1. customThe cooling bath was removed
  2. temperatureto warm to room temperature
  3. temperatureThereafter, the reaction mixture was cooled again to 0° C.
  4. customa precipitate being formed
  5. customThe cooling bath was removed again
  6. temperatureto warm to room temperature
  7. stirringwhile being subsequently stirred for a further hour
  8. temperatureThe solution was then cooled again to -20° C.
  9. additionWhen the addition
  10. customthe cooling bath was removed again
  11. customrose to room temperature
  12. stirringthe solution was subsequently stirred for a further 1.5 hours
  13. temperatureThe suspension was then cooled again to 0° C.
  14. temperatureThe resulting suspension was warmed to room temperature
  15. stirringstirred for a further 1.5 hours
  16. filtrationsubsequently filtered through a frit
  17. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-082762372e8843a5a865679b02b95b4b
Source dataset
uspto-grants-2000_12
Patent number
US06156857

Reaction notes

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