Triphenylphosphine → 4-[(Triphenylphosphoranylidene)amino]-5-ethoxy-dihydrofuran-2-one

HRID 2215955Notes

Reaction equation

HRID 2215955 reaction equation
[N:1]([CH:4]1[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH2:5]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>C1(C)C=CC=CC=1>[C:26]1([P:19](=[N:1][CH:4]2[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH2:5]2)([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

4

Reactant 2

HCID 11776TriphenylphosphineHCID 112982094-Azido-5-ethoxy-dihydrofuran-2-one

Product 1

HCID 865885854-[(Triphenylphosphoranylidene)amino]-5-ethoxy-dihydrofuran-2-oneYield 102.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-azido-5-ethoxy-dihydrofuran-2-one (0.05 g, 0.29 mmol) and triphenylphosphine (0.078 g, 0.29 mmol) in toluene (5 mL) was stirred at room temperature under nitrogen for 5 h. The solvent was evaporated to afford 4-[(triphenylphosphoranylidene)amino]-5-ethoxy-dihydrofuran -2-one (0.12 g, 100% yield) as an off-white, waxy solid. 1H-NMR (500 MHz, CDCl3) δ 7.50 (m, 6H), 7.40 (m, 3H), 7.33 (m, 6H), 5.08 (d, J=3.1 Hz, 1H), 3.63 (m, 1H), 3.23 (m, 1H), 2.50 (dd, J=17.1, 5.9 Hz, 1H), 2.27 (dd, J=17.1, 5.9 Hz, 1H), 0.91 (t, J=7.0 Hz, 3H) ppm.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7d51af438cba47ed8a3c76994fe9ea2d
Source dataset
uspto-grants-2006_09
Patent number
US07109357B2

Reaction notes

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