Triphenylphosphine → Triphenylphosphine Oxide

HRID 918898Notes

Reaction equation

HRID 918898 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=[O:23]>O1CCCC1>[P:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:23]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5 (94 mg, 0.58 mmol), 31 (120 mg, 0.49 mmol), and triphenylphosphine (321 mg, 1.23 mmol) in tetrahydrofuran (10 mL) at 65° C. under nitrogen was added diisopropyl azodicarboxylate (247 mg, 1.23 mmol). The mixture was cooled to room temperature, concentrated, and purified by chromatography (silica gel, 0-100% ethyl acetate/hexanes) to give crude 32 (230 mg, contained Ph3PO).

Workup

  1. concentrationconcentrated
  2. custompurified by chromatography (silica gel, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f9f575d5829d42449208107804b1cbaf
Source dataset
uspto-grants-2016_03
Patent number
US09271978B2

Reaction notes

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