Triphenylphosphine → HCID 11961748, compound

HRID 392908Notes

Reaction equation

HRID 392908 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]1[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][C:29]=1[CH2:30][N:31]=[N+]=[N-])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[NH4+]>C1COCC1>[CH2:20]([O:27][C:28]1[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][C:29]=1[CH2:30][NH2:31])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 14923Ammonium HydroxideHCID 22661867HCID 22661867, compound

Product 1

HCID 11961748HCID 11961748, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (1.64 g, 6.24 mmol) was added to a solution of 2-benzyloxy-5-cyano-benzylazide (1.1 g, 4.16 mmol) in anhydrous THF (10 mL) at 0° C. After 1 hour, ammonium hydroxide (0.5 mL) was added and the mixture was warmed to room temperature and stirred overnight. The mixture was concentrated and the residue purified by flash chromatography (3% methanol/dichloromethane) to afford 677 mg (69%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.6-7.3 (m, 7H); 6.95 (d, 1H, J=9.1 Hz); 5.18 (s, 2H); 3.9 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by flash chromatography (3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-27140a9d3977445ca265dd4987084230
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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