Triphenylphosphine Oxide → HCID 56933439, compound

HRID 1184339Notes

Reaction equation

HRID 1184339 reaction equation
[F:1][C:2]1([F:26])[O:7][C:6]2[CH:8]=[C:9]([F:21])[C:10]([NH:12]/[N:13]=[CH:14]/[C:15](=O)[C:16]([F:19])([F:18])[F:17])=[CH:11][C:5]=2[N:4]([CH2:22][C:23]#[CH:24])[C:3]1=[O:25].[C:27]([CH2:32][CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=[O:28].C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1([F:26])[C:3](=[O:25])[N:4]([CH2:22][C:23]#[CH:24])[C:5]2[CH:11]=[C:10]([N:12]3[C:27](=[O:28])[C:32]([CH3:33])=[C:15]([C:16]([F:19])([F:18])[F:17])[CH:14]=[N:13]3)[C:9]([F:21])=[CH:8][C:6]=2[O:7]1

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoateHCID 87173926HCID 87173926, compound

Product 1

HCID 56933439HCID 56933439, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred yellow suspension of (E)-2,2,7-trifluoro-4-(prop-2-ynyl)-6-(2-(3,3,3-trifluoro-2-oxopropylidene)hydrazinyl)-2H-benzo[b][1,4]oxazin-3-one (1399 mg, 3.69 mmol) in dry toluene (20 ml) was added (carbethoxyethylidene)triphenylphosphorane (1738 mg, 4.80 mmol), resulting in a clear orange/red solution. The reaction was continued overnight at reflux under Dean-Stark conditions, while conducting aezotropic dehydration. Thereupon the reaction mixture was concentrated in vacuo to yield 2.99 g of crude product containing ca. 50% triphenylphosphine oxide. The crude product was chromatographed over silica (9:1→1:1 heptane/ethyl acetate) to yield 1.08 g of product (ca. 89% purity). Recrystallisation from diisopropyl ether/heptane gave the title compound as a white powder (purity>99%).

Workup

  1. customresulting in a clear orange/red solution
  2. temperatureat reflux under Dean-Stark conditions
  3. concentrationThereupon the reaction mixture was concentrated in vacuo
  4. customto yield 2.99 g of crude product
  5. customThe crude product was chromatographed over silica (9:1→1:1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5c74ce43214c42a5b0a76fd1e297cf5b
Source dataset
uspto-grants-2014_03
Patent number
US08669208B2

Reaction notes

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