Toluene → Triphenylphosphine Oxide

HRID 1484023Notes

Reaction equation

HRID 1484023 reaction equation
CC1C=CC([N+]([O-])=[O:9])=CC=1O.CN(C)CCO.[C:18]1([P:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[C:31]1([P:24](=[O:9])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 935762-Methyl-5-nitrophenolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As another non-limiting example, 2-methyl-5-nitrophenol (2.00 g, 13.07 mmol), N,N-dimethylethanolamine (1.31 mL, 13.07 mmol) and triphenylphosphine (4.46 g, 16.99 mmol) were placed in a 100 mL round-bottomed flask under nitrogen. 40 mL of anhydrous THF were added via syringe at 0° C. After stirring the reaction mixture at this temperature for 10 minutes, 7.32 mL of a solution of diethylazodicarboxylate 40% in toluene (2.93 g, 16.99 mmol) were added via syringe. The reaction was warmed to room temperature and stirred under nitrogen for two hours. The solvents were removed under vacuum. Triphenylphosphine oxide formed during the reaction was precipitated in a mixture of ethyl acetate/hexane and filtrated. The crude was then purified by flash chromatography (0 to 2% of MeOH in DCM) to afford 10 (2.11 g, 70%) as a yellow oil.

Workup

  1. stirringstirred under nitrogen for two hours
  2. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-979eb49c8ed64bca9e686a371bce323a
Source dataset
uspto-grants-2016_08
Patent number
US09421211B2

Reaction notes

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