1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22464525, compound

HRID 1935442Notes

Reaction equation

HRID 1935442 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:6]=1[CH2:7]O.C1(P([N:30]=[N+:31]=[N-:32])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:6]=1[CH2:7][N:30]=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 431419322-(2,2,2-Trifluoroethoxy)-5-chlorobenzyl alcohol

Product 1

HCID 22464525HCID 22464525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2,2,2-trifluoroethoxy)-5-chlorobenzyl alcohol (1.9 g, 7.9 mmol) in THF (20 mL) at 0° C. was added diphenyl phosphoryl azide (2.2 mL, 10.2 mmol) followed by DBU (1.5 mL, 10.0 mmol). The reaction mixture was allowed to warm to room temperature overnight following which the solvent was removed under reduced pressure. The residue was partitioned between ether and water and the organic layer dried over sodium sulfate. Filtration, concentration and purification by flash chromatography (19:1 hexane/ether) gave the azide as a white solid: 1H NMR (CDCl3) δ7.31 (m, 2H), 6.82 (d, J=8.8 Hz, 1H), 4.40 (m, 4H).

Workup

  1. customwas removed under reduced pressure
  2. customThe residue was partitioned between ether and water
  3. dry with materialthe organic layer dried over sodium sulfate
  4. filtrationFiltration, concentration and purification by flash chromatography (19:1 hexane/ether)

Sources & evidence

ORD record
ord-0f2609cb8b0e478e8a6dcf6e57f9fb41
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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