2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane

Base Information

• Chemical Name: 2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane
• CAS No.: 149209-47-2
• Molecular Formula: C12H13F3O2
• Molecular Weight: 246.229
• Mol file: 149209-47-2.mol

Synonyms:2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyran;

Chemical Property of 2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane

Chemical Property:

• Boiling Point: 297.4±40.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.228±0.06 g/cm3(Predicted)
• LogP: 3.61080

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane

There total 1 articles about 2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane 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: 95.0%

3,4-dihydro-2H-pyran (110-87-2) + 2-(trifluoromethyl)phenol (444-30-4) → 2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane (149209-47-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene; at 60 ℃; for 16h;

DOI:10.1016/j.bmcl.2009.07.135

Reference yield: 96.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + 2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane (149209-47-2) → 2-(tetrahydro-2H-pyran-2-yloxy)-3-(trifluoromethyl)benzaldehyde (873011-15-5) + 2-hydroxy-3-(trifluoromethyl)benzaldehyde (336628-67-2)

Guidance literature:

2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; diethyl ether; at -20 - 20 ℃; for 1.33333h;

N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; at -30 - -20 ℃; for 1h;

Reference yield:

2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane (149209-47-2) → 1-[4-(tert-Butyl-dimethyl-silanyloxy)-3,5-bis-trifluoromethyl-phenyl]-hex-5-yn-1-one (1026274-93-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) BuLi, 2) iodine / 1) THF, -78 deg C, 30 min, 2) a) THF, -78 deg C, 10 min, b) to room temperature

2: 47 percent / dimethylformamide; hexamethylphosphoric acid triamide / 1.5 h / 60 °C

3: Br₂, Fe powder / CCl₄ / 2 h / 60 °C

4: 4-(dimethylamino)pyridine, triethylamine / tetrahydrofuran / 2 h / Ambient temperature

5: 1) a) Mg, 1,2-dibromomethane, c) ZnCl₂ / 2) tetrakis(triphenylphosphine)palladium / 1) THF, a) 45 deg C, 10 min, b) ultrasonic bath, room temperature, 1 h, c) 25 deg C, 15 min, 2) room temperature, 1 h

With dmap; n-butyllithium; 1,2-dibromomethane; bromine; iodine; iron; magnesium; triethylamine; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;

DOI:10.1021/jo00061a048

upstream raw materials:

3,4-dihydro-2H-pyran

2-(trifluoromethyl)phenol

Downstream raw materials:

2-iodo-6-(trifluoromethyl)phenol

2,6-bis(trifluoromethyl)phenol

2,6-bis(trifluoromethyl)-4-bromophenol

2,6-bis(trifluoromethyl)-4-bromophenol TBDMS ether

Refernces

• 1、 Shao, Pengcheng P.,Ye, Feng,Weber, Ann E.,Li, Xiaohua,Lyons, Kathryn A.,Parsons, William H.,Garcia, Maria L.,Priest, Birgit T.,Smith, McHardy M.,Felix, John P.,Williams, Brande S.,Kaczorowski, Gregory J.,McGowan, Erin,Abbadie, Catherine,Martin, William J.,McMasters, Daniel R.,Gao, Ying-Duo. "Discovery of isoxazole voltage gated sodium channel blockers for treatment of chronic pain". scheme or table. p. 5334 - 5338. Retrieved 2010/04/26.