Tetrahydrofuran → HCID 178506801, compound

HRID 2166732Notes

Reaction equation

HRID 2166732 reaction equation
C1(C(C2C=CC=CC=2)=C)C=CC=CC=1.C1COCC1.[Li:20]CCCC.[C:25]1([CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][Li])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCCCCC.CO>[C:25]1([C:31]([Li:20])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 107401,1-DiphenylethyleneHCID 178418339ButyllithiumHCID 178506866HCID 178506866, compound

Product 1

HCID 178506801HCID 178506801, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent2×

Procedure

Into a flask equipped with a mechanical stirrer and under a constant flow of argon was injected 0.8 ml (0.0044 mole) of 1,1-diphenylethylene followed by 100 ml of THF and 0.0038 mole of 1.6 M n-BuLi in hexane. The blood red color of diphenylhexyllithium developed immediately and the solution was stirred at room temperature for five minutes. It was then cooled to -74° C. and 3.2 ml (0.024 mole) of GMA was added dropwise from a hypodermic syringe. The red color discharged to a faint yellow after about 0.5 ml had been added, and the temperature rose to -70° C. until addition was complete (about 5 minutes). The temperature then returned to -74° C. and 10 ml (0.09 mole) of MMA was added dropwise at such a rate that the temperature did not exceed -69° C. (about 15 minutes). Following that, another 3.2 ml of GMA was added, the solution was stirred at -72° C. for 10 min, 1 ml of methanol was injected and the solution was poured into 1 liter of hexane. The stringy white polymer was collected and dried; yield, 15.0 g (97%).

Workup

  1. customInto a flask equipped with a mechanical stirrer and under a constant flow of argon
  2. temperatureIt was then cooled to -74° C.
  3. addition3.2 ml (0.024 mole) of GMA was added dropwise from a hypodermic syringe
  4. additionhad been added
  5. additionthe temperature rose to -70° C. until addition
  6. custom(about 5 minutes)
  7. customthen returned to -74° C.
  8. addition10 ml (0.09 mole) of MMA was added dropwise at such a rate that the temperature
  9. customdid not exceed -69° C.
  10. custom(about 15 minutes)
  11. additionwas added
  12. stirringthe solution was stirred at -72° C. for 10 min
  13. customThe stringy white polymer was collected
  14. customdried
  15. customyield

Sources & evidence

ORD record
ord-1256e25770ef4f13a46afae95714528a
Source dataset
uspto-grants-1983_06
Patent number
US04388448

Reaction notes

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