1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58496628, compound

HRID 659974Notes

Reaction equation

HRID 659974 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH2:10][CH2:11][CH3:12])=[CH:5][CH:4]=1.C1(P([N:30]=[N+:31]=[N-:32])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1.CCOCC.O>[N:30]([CH:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=1)[CH2:10][CH2:11][CH3:12])=[N+:31]=[N-:32]

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 14994241HCID 14994241, compound

Product 1

HCID 58496628HCID 58496628, compoundYield 54.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[4-(trifluoromethyl)phenyl]butan-1-ol (1.4 , 6.4 mmol) and diphenylphosphoryl azide (2.8 ml, 12.8 mmol) in THF (6 mL) cooled to −10° C. under N2 was treated with DBU (1.9 mL, 12.8 mmol). The resulting solution was stirred at room temperature for 20 hours and then diluted with a mixture of ether and H2O. The organic phase was dried and concentrated and the residue purified by column chromatography using hexane:diethyl ethyl acetate (10:1) as eluent to furnish pure azide (0.85 g, 54%).

Workup

  1. customThe organic phase was dried
  2. concentrationconcentrated
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-aa2da689746843a5af284e8e75f84673
Source dataset
uspto-grants-2011_12
Patent number
US08084456B2

Reaction notes

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