Triphenylphosphine → Triphenylphosphine Oxide

HRID 918900Notes

Reaction equation

HRID 918900 reaction equation
CC1C(C2C=C(NC(=O)C)C(=O)NC=2)=C(C)[O:4]N=1.N1C2C(=C(CO)C=CC=2)C=C1.[C:30]1([P:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[P:36]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 27734571H-indol-4-ylmethanolHCID 90234246HCID 90234246, compound

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 31 (700 mg, 2.83 mmol), (1H-indol-4-yl)methanol (1.25 g, 8.50 mmol), and triphenylphosphine (2.97 g, 11.3 mmol) in tetrahydrofuran (30 mL) at 60° C. under nitrogen atmosphere was added diisopropyl azodicarboxylate (1.43 g, 7.07 mmol). The mixture was cooled to room temperature, concentrated, and purified by chromatography (silica gel, 0-100% ethyl acetate/hexanes) to give crude 59 (1.94 g, contained Ph3PO).

Workup

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

Sources & evidence

ORD record
ord-c5e09381545241c29db297b8a82e56b5
Source dataset
uspto-grants-2016_03
Patent number
US09271978B2

Reaction notes

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