Iodine → HCID 86602382, compound

HRID 857817Notes

Reaction equation

HRID 857817 reaction equation
II.[C:3]1([CH3:25])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]O)=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].C([O:28][P:29]([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])C>>[C:3]1([CH3:25])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][P:29](=[O:28])([O:30][CH2:31][CH3:32])[O:33][CH2:34][CH3:35])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

Participants

4

Reactant 3

HCID 807IodineHCID 31215Triethyl phosphiteHCID 69618705HCID 69618705, compound

Product 1

HCID 86602382HCID 86602382, compound

Conditions

Temperature
25 °C

Procedure

Iodine (6.6 mmol) was added to a mixture of 4-(N,N-di-tolylamino)-benzyl alcohol (6.6 mmol) and triethylphosphite (10 mL) at 0° C. The reaction was allowed to warm to 25° C. and stirred for two hours. Excess triethylphosphite was distilled away from the reaction under reduced pressure, and the residue was partitioned between ether and water. The organic extracts were dried and concentrated to an oil, which was then purified by column chromatography to yield 1.6 g of diethyl 4-(N,N-di-tolylamino)-benzylphosphonate. The product was a pale, viscous oil. H1 NMR and mass spectra data were consistent with the structure.

Workup

  1. distillationExcess triethylphosphite was distilled away from the reaction under reduced pressure
  2. customthe residue was partitioned between ether and water
  3. customThe organic extracts were dried
  4. concentrationconcentrated to an oil, which
  5. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-7fb766e2effe46fc88d90c22959bc975
Source dataset
uspto-grants-2006_12
Patent number
US07147938B2

Reaction notes

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