Triphenylphosphine → Triphenylphosphine Oxide

HRID 2215963Notes

Reaction equation

HRID 2215963 reaction equation
[N:1]([C:4]1[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH:5]=1)=[N+]=[N-].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1.O.ClCCl>[NH2:1][C:4]1[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH:5]=1.[C:26]1([P:19](=[O:7])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 2

HCID 11776TriphenylphosphineHCID 219532314-azido-5-ethoxy-5H-furan-2-one

Product 2

HCID 13097Triphenylphosphine OxideYield 304.5%HCID 219532364-amino-5-ethoxy-5H-furan-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-azido-5-ethoxy-5H-furan-2-one (0.10 g, 0.59 mmol) and triphenylphosphine (0.15 g, 0.59 mmol) in tetrahydrofuran (5 mL) and water (0.5 mL) was stirred for 20 h at room temperature, followed by 3d at 65° C. under nitrogen. The reaction was diluted with dichloromethane, washed with water, dried over sodium sulfate and evaporated to afford 4-amino-5-ethoxy-5H-furan-2-one in a mixture with triphenylphosphine oxide (0.25 g, 100% yield).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-a5dacd995bfa4952acb766969cd0eb4a
Source dataset
uspto-grants-2006_09
Patent number
US07109357B2

Reaction notes

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