(2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone

Base Information

• Chemical Name: (2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone
• CAS No.: 174951-49-6
• Molecular Formula: C₁₄H₁₇FO₃
• Molecular Weight: 252.286
• Mol file: 174951-49-6.mol

Synonyms:(2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone

Chemical Property of (2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone

There total 1 articles about (2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone 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: 55.0%

o-fluorobromobenzene (1072-85-1) + 4-<(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl>morpholine (135206-86-9) → (2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone (174951-49-6)

Guidance literature:

With magnesium; In tetrahydrofuran; at 30 - 35 ℃; for 2h;

DOI:10.1248/cpb.43.441

Reference yield: 97.0%

(2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone (174951-49-6) → (S)-1-(2-Fluorophenyl)-2-hydroxypropanone (174563-15-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 55 ℃; for 2.5h;

DOI:10.1248/cpb.47.360

Reference yield:

(2S)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-propiophenone (174951-49-6) → 1-[(1R,2R)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2-imidazolidinone

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / pyridinium p-toluenesulfonate / ethanol / 2.5 h / 55 °C

2: 88 percent / i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -30 °C

3: 1.) NaH, 1-methyl-2-pyrrolidone / 1.) RT, 15 min, 2.) THF, -20 deg C, 10 min

4: 1.) Mg, MeI / 1.) THF, from 45 deg C to 50 deg C, 3 h, 2.) THF, 0 deg C, 20 min

5: 89 percent / 30 percent aq. H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 1.5 h / 70 - 80 °C

6: 100 percent / Et₃N / ethyl acetate / 0.5 h / 0 °C

7: 75 percent / K₂CO₃ / dimethylformamide / 5 h / 90 °C

8: H₂, AcOH / 10 percent Pd/C / 3 h / 50 °C / 760 Torr

With 1-methyl-pyrrolidin-2-one; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; magnesium; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.47.360

upstream raw materials:

o-fluorobromobenzene

4-<(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl>morpholine

Downstream raw materials:

(S)-1-(2-Fluorophenyl)-2-hydroxypropanone

(2S)-2'-fluoro-2-trifluoromethanesulfonyloxypropiophenone

1-[(1R)-2-(2-fluorophenyl)-2-oxo-1-methylethyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone

1-[(1R)-2-(2-fluorophenyl)-2-oxo-1-methylethyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone

Refernces

• 1、 -. "Azole compounds, their production and use". . . Retrieved 2008/06/13.