1-Cyclopropyl-2-(triphenylphosphoranylidene)-ethanone

Base Information

• Chemical Name: 1-Cyclopropyl-2-(triphenylphosphoranylidene)-ethanone
• CAS No.: 7691-76-1
• Molecular Formula: C23H21OP
• Molecular Weight: 344.393
• Hs Code.: 2920907090
• Mol file: 7691-76-1.mol

Synonyms:cyclopropylcarbonylmethylenetriphenylphosphorane;cyclopropylcarbonyl iodide;Triphenyl-cyclopropylcarbonylmethylen-phosphoran;Cyclopropanecarbonyliodide;

Chemical Property of 1-Cyclopropyl-2-(triphenylphosphoranylidene)-ethanone

Chemical Property:

• Boiling Point: 511.5±33.0 °C(Predicted)
• PSA: 26.88000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 3.76180
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

1-Cyclopropyl-2-(triphenylphosphoranylidene)-ethanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Cyclopropyl-2-(triphenylphosphoranylidene)-ethanone

There total 7 articles about 1-Cyclopropyl-2-(triphenylphosphoranylidene)-ethanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide (112849-15-7) → 1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one (7691-76-1)

Guidance literature:

With sodium hydroxide; In dichloromethane; water;

DOI:10.1016/S0040-4020(01)86903-9

Reference yield:

triphenylphosphinocyclopropylcarbonylmethylene bromide → 1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one (7691-76-1)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 2h; Time; Autoclave; Large scale;

Reference yield:

2-bromo-1-cyclopropylethan-1-one (69267-75-0) + triphenylphosphine (603-35-0) → 1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one (7691-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 1 h / Reflux

2: sodium hydroxide

With sodium hydroxide; In tetrahydrofuran;

upstream raw materials:

Triphenyl-{1-[2-(triphenyl-λ⁵-phosphanylidene)-acetyl]-cyclopropyl}-phosphonium; bromide

(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide

Cyclopropyl methyl ketone

triphenylphosphine

Downstream raw materials:

20(R),3(R)-(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10⁽¹⁹⁾-triene

1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3’-cyclopropyl-3’-oxypropyl-1’(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene

(1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene

Refernces

• 1、 Xie, Peizhong,Fu, Weishan,Cai, Xinying,Sun, Zuolian,Wu, Ying,Li, Shuangshuang,Gao, Cuiqing,Yang, Xiaobo,Loh, Teck-Peng. "A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions". supporting information. p. 7055 - 7059. Retrieved 2019/09/12.
• 2、 Aitken, David J.,Caboni, Pierluigi,Cuccu, Federico,Frongia, Angelo,Luridiana, Alberto,Secci, Francesco,Serusi, Lorenzo. "Tandem Wittig Reaction-Ring Contraction of Cyclobutanes: A Route to Functionalized Cyclopropanecarbaldehydes". supporting information. . Retrieved 2019/10/08.