Triphenylphosphine → 1-(3-Phenylbenzofuran-2-yl)ethanamine

HRID 242856Notes

Reaction equation

HRID 242856 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH:23]([C:25]1[O:26][C:27]2[CH:39]=[CH:38][CH:37]=[CH:36][C:28]=2[C:29]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:24])=[N+]=[N-]>C1COCC1.O>[C:30]1([C:29]2[C:28]3[CH:36]=[CH:37][CH:38]=[CH:39][C:27]=3[O:26][C:25]=2[CH:23]([NH2:20])[CH3:24])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 866688702-(1-Azidoethyl)-3-phenylbenzofuran

Product 1

HCID 681571391-(3-Phenylbenzofuran-2-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Triphenylphosphine (231 mg, 0.883 mmol) was added to a solution of 2-(1-azidoethyl)-3-phenylbenzofuran (186 mg, 0.706 mmol) in THF (9 mL) and water (1 mL). The mixture was heated at 60° C. for 2 h and then cooled to RT. Volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) affording 1-(3-phenylbenzofuran-2-yl)ethanamine as an oil (327 mg, quantitative). LCMS: RT 2.21 min [M−NH2]+ 221.1

Workup

  1. temperaturecooled to RT
  2. customVolatiles were removed under reduced pressure
  3. customthe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-563244ca3b9f4444b1f3f95d4b225fc0
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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