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

HRID 379512Notes

Reaction equation

HRID 379512 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 (×4), and the combined organic layers were washed with H2O (×2), 0.5N HCl (×2) and brine (×2), dried over MgSO4 and evaporated in vacuo. 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), 5.0 (2H), 3.83 (3H, OMe), 1.8-2.2 (4H).

Workup

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

Sources & evidence

ORD record
ord-a5d026940fd449d48e017e9c4e6a7526
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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