Triphenylphosphine → HCID 86737156, compound

HRID 1856440Notes

Reaction equation

HRID 1856440 reaction equation
[CH2:1]1[CH2:18][O:17][CH:9]([CH2:10][CH:11]2[O:16][CH2:15][CH2:14][O:13][CH2:12]2)[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][I:8])[O:2]1.[C:19]1([P:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C.CCN(C(C)C)C(C)C>[I-:8].[CH2:1]1[CH2:18][O:17][CH:9]([CH2:10][CH:11]2[O:16][CH2:15][CH2:14][O:13][CH2:12]2)[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][P+:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:2]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 70593462HCID 70593462, compound

Product 1

HCID 86737156HCID 86737156, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 4.13 g (11.2 mmol) of 5,8-bis(ethylenedioxy)nonyl iodide and 2.93 g (11.2 mmol) of triphenyl phosphine in 25 ml of acetonitrile was buffered with a few drops of Hunig's Base and heated under nitrogen at 65° for 24 hours. The solvent was removed in vacuo until the resulting gum began to foam. This viscous gum was taken up in 25 ml of 3-pentanone and the resulting solution was seeded with a crystal of the salt and allowed to stand until crystallization was complete. Filtration afforded 4.98 g of salt. The mother liquors were placed in the freezer overnight and another 0.64 g of salt crystallized. Yield (5.62 g, 80%).

Workup

  1. temperatureheated under nitrogen at 65° for 24 hours
  2. customThe solvent was removed in vacuo until the resulting gum
  3. customto stand until crystallization
  4. filtrationFiltration

Sources & evidence

ORD record
ord-fd908730304b4c0993d5ca6739a3f45c
Source dataset
uspto-grants-1980_08
Patent number
US04219489

Reaction notes

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