Toluene → Triphenylphosphine

HRID 222640Notes

Reaction equation

HRID 222640 reaction equation
[C:1]1([P:7](N=[N+]=[N-])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N12CCCN=[C:24]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2.C1(C)C=CC=CC=1>O1CCCC1.O>[C:1]1([P:7]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 11776Triphenylphosphine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, compounds of formula (16) can be (a) treated with diphenylphosphorylazide and 1,8-diazabicyclo[5.4.0]undec-7-ene in a solvent such as, but not limited to toluene, at a temperature of about 0° C. to about 50° C.; and (b) treated with the asides obtained from step (a) with triphenylphosphine in a mixture of tetrahydrofuran and water and at about the reflux temperature of the solvent, to provide compounds of formula (18).

Sources & evidence

ORD record
ord-de1b4f8b707d449e9fb7833afd031ae7
Source dataset
uspto-grants-2012_06
Patent number
US08207350B2

Reaction notes

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