Water → 5-Azido-5-(2-methoxyphenyl)-1-pentene

HRID 377155Notes

Reaction equation

HRID 377155 reaction equation
O[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH2:3][CH2:4][CH:5]=[CH2:6].C1(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1.O>C1(C)C=CC=CC=1>[N:29]([CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH2:3][CH2:4][CH:5]=[CH2:6])=[N+:30]=[N-:31]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 158847211-(2-Methoxyphenyl)pent-4-en-1-ol

Product 1

HCID 158847225-Azido-5-(2-methoxyphenyl)-1-pentene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of crude 5-hydroxyl-5-(2-methoxyphenyl)-1-pentene, prepared as described above, in toluene (150 mL) at 0° to 40° C. was added diphenylphosphoryl azide (25.86 mL, 120 mmol) followed by DBU (17.95 mL, 120 mmol) and the resulting reaction mixture was stirred at room temperature (20° C. to 25° C.) for 28 hours. H2O was added, the aqueous layer was extracted with ether (x4), and the combined organic layers were washed with H2O (x2), 0.5N HCl (x2) and brine (x2), dried over MgSO4 and evaporated in vacuao. The crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes) to provide the title compound as a colorless liquid (14 g). 1H NMR (CDCl3, 400 MHz) δ: 6.8-7.4 (4H), 5.8 (1H) (2H), 3.83 (3H, OMe), 1.8-2.2 (4H), 5.0

Workup

  1. customat 0° to 40° C.
  2. customthe resulting reaction mixture
  3. extractionthe aqueous layer was extracted with ether (x4)
  4. washthe combined organic layers were washed with H2O (x2), 0.5N HCl (x2) and brine (x2)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuao
  7. customThe crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes)

Sources & evidence

ORD record
ord-b117afc933e84f13b8d54ce2de100d89
Source dataset
uspto-grants-2000_02
Patent number
US06025350

Reaction notes

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