1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(Azidomethyl)-4-methoxybenzonitrile

HRID 1935438Notes

Reaction equation

HRID 1935438 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5]O)#[N:2].C1(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[C:1]([C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH2:5][N:27]=[N+:28]=[N-:29])#[N:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 45091016HCID 45091016, compound

Product 1

HCID 224645382-(Azidomethyl)-4-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-cyano-5-methoxybenzyl alcohol (1.8 g, 11 mmol) in THF (50 mL) was cooled to 0° C. and then treated sequentially with diphenylphosphoryl azide (2.8 mL, 13 mmol) and DBU 1.9 mL, 13 mmol), the former added in one portion and the latter dropwise. The reaction mixture was allowed to warm gradually to room temperature and to then stir there overnight. The solvent was removed and the residue partitioned between ethyl acetate and water. The organic phase was washed with dilute citric acid, then brine and dried (Na2SO4). The solvent was removed in vacuo and the residue purified by column chromatography eluting with 4:1:1 hexane/chloroform/ethyl acetate to give the product as a yellow oil: 1H NMR (CDCl3) δ7.62 (d, J=8.6 Hz, 1H), 7.02 (d, J=2.6 Hz, 1H), 6.92 (dd, J=2.6, 8.6 Hz, 1H), 4.59 (s, 2H), 3.89 (s, 3H).

Workup

  1. additionformer added in one portion
  2. customThe solvent was removed
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic phase was washed with dilute citric acid
  5. dry with materialbrine and dried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by column chromatography
  8. washeluting with 4:1:1 hexane/chloroform/ethyl acetate

Sources & evidence

ORD record
ord-4a7768417e0b49f0b72e6fa9d6d6c486
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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