Water → HCID 57978289, compound

HRID 1866520Notes

Reaction equation

HRID 1866520 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:22][C:23](=[O:36])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH2:32][N:33]=[N+]=[N-])[CH:26]=1)[CH3:21].O>O1CCCC1>[CH2:20]([O:22][C:23](=[O:36])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][CH2:32][NH2:33])[CH:26]=1)[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57978188HCID 57978188, compound

Product 1

HCID 57978289HCID 57978289, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Triphenylphosphine (3.88 g, 23.3 mmol) was added in one portion to a stirred solution of ethyl[3-(2-azidoethyl)phenyl]acetate (Preparation 57) (3.88 g, 16.6 mmol) in tetrahydrofuran (100 ml) at room temperature under nitrogen. The reaction was stirred for 18 hours and water (5 ml) added and the reaction heated at 50° C. for 4 hours, the reaction was cooled to room temperature and the solvent removed in vacuo. The residue was dissolved in saturated aqueous sodium hydrogen carbonate (40 ml) and the aqueous extracted with dichloromethane (3×50 ml). The combined organics were dried (sodium sulfate), the solvent removed in vacuo and the residue purified by flash column chromatography on silica gel eluting with dichlromethane:methanol (95:5, by volume) to give the title compound as a colourless oil (3.11 g). 1H NMR (400 MHz, CDCl3): δ 7.26-7.22 (1H, t), 7.13-7.08 (3H, t), 4.16-4.11 (2H, m), 3.58 (2H, s), 2.96-2.93 (2H, t), 2.74-2.71 (2H, t), 1.25-1.22 (3H, t) ppm. LRMS (electrospray): M/Z [M+H]+ 208, [M+NA]+ 230, [M−H]− 206.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in saturated aqueous sodium hydrogen carbonate (40 ml)
  4. extractionthe aqueous extracted with dichloromethane (3×50 ml)
  5. dry with materialThe combined organics were dried (sodium sulfate)
  6. customthe solvent removed in vacuo
  7. customthe residue purified by flash column chromatography on silica gel eluting with dichlromethane

Sources & evidence

ORD record
ord-2f97434c5a924feeac6785b267157630
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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