Carbon Tetrachloride → HCID 20095014, compound

HRID 1770153Notes

Reaction equation

HRID 1770153 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[CH2:25]([CH:33]1[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:42](=O)[NH2:43])[CH:39]=2)[CH2:34]1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C1COCC1>[CH2:25]([CH:33]1[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[C:38]([C:42]#[N:43])[CH:39]=2)[CH2:34]1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 20095016HCID 20095016, compound

Product 1

HCID 20095014HCID 20095014, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Subsequently, 8.71 g (33.2 mM) of triphenylphosphine, 25 ml of carbon tetrachloride and 15 ml of THF were placed in 200 ml-three necked flask. Under stirring at room temperature, 4.55 g (16.6 mM) of the above-prepared 2-octyl-5-carbamoylindan was gradually added to the above mixture, followed by washing with 10 ml, of THF and stirring for 3 hours at 45°-50.4° C. to precipitate a crystal. After the reaction, the crystal was removed from the reaction mixture by filtration and the filtrate was evaporated under reduced pressure to obtain a residue. The residue was purified silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized from methanol to obtain 4.24 g of 2-octyl-5-cyanoindan (Yield: 99.8%).

Workup

  1. washby washing with 10 ml, of THF
  2. stirringstirring for 3 hours at 45°-50.4° C.
  3. customto precipitate a crystal
  4. customAfter the reaction
  5. customthe crystal was removed from the reaction mixture by filtration
  6. customthe filtrate was evaporated under reduced pressure
  7. customto obtain a residue
  8. customThe residue was purified silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d567fd3ddd164d3980531c2018ea7a2c
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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