α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate

Base Information

• Chemical Name: α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate
• CAS No.: 127308-50-3
• Molecular Formula: C₂₀H₂₅F₃O₃
• Molecular Weight: 370.412
• Mol file: 127308-50-3.mol

Synonyms:

Chemical Property of α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate

There total 9 articles about α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate 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:

(1S,3R,5R)-methyl 3-(hydroxymethyl)-4,4,5-trimethylcyclopentanecarboxylate (127308-42-3) → α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate (127308-50-3)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole, 4-(dimethylamino)pyridine / tetrahydrofuran / 3 h / Ambient temperature

3: 1) m-chloroperoxybenzoic acid, 2) diisopropylamine / 1) CH₂Cl₂, -10 deg C, 0.5 h, 2) reflux, 0.5 h

4: lithium ethoxyaluminium hydride / tetrahydrofuran / 0 °C

5: Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

6: Li / liquid ammonia; tetrahydrofuran; methanol / 1 h / Heating

7: tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

8: 0.1 mg / pyridine / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium monoethoxyaluminum hydride; tetrabutyl ammonium fluoride; lithium; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ammonia;

DOI:10.1021/jo00300a021

Reference yield:

(1S,3R,5R)-3-(hydroxymethyl)-4,4,5-trimethylcyclopentanecarboxylic acid (127308-41-2) → α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate (127308-50-3)

Guidance literature:

Multi-step reaction with 9 steps

1: diethyl ether; methanol / 0.5 h / Ambient temperature

2: imidazole, 4-(dimethylamino)pyridine / tetrahydrofuran / 3 h / Ambient temperature

4: 1) m-chloroperoxybenzoic acid, 2) diisopropylamine / 1) CH₂Cl₂, -10 deg C, 0.5 h, 2) reflux, 0.5 h

5: lithium ethoxyaluminium hydride / tetrahydrofuran / 0 °C

6: Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

7: Li / liquid ammonia; tetrahydrofuran; methanol / 1 h / Heating

8: tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

9: 0.1 mg / pyridine / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium monoethoxyaluminum hydride; tetrabutyl ammonium fluoride; lithium; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia;

DOI:10.1021/jo00300a021

Reference yield:

(3R,5R)-methyl 3-<<(tert-butyldimethylsilyl)oxy>methyl>-4,4,5-trimethylcyclopentenecarboxylate (127308-46-7) → α-necrodol α-methoxy-α-(trifluoromethyl)phenylacetate (127308-50-3)

Guidance literature:

Multi-step reaction with 5 steps

1: lithium ethoxyaluminium hydride / tetrahydrofuran / 0 °C

2: Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

3: Li / liquid ammonia; tetrahydrofuran; methanol / 1 h / Heating

4: tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / Ambient temperature

5: 0.1 mg / pyridine / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; lithium monoethoxyaluminum hydride; tetrabutyl ammonium fluoride; lithium; triethylamine; In tetrahydrofuran; methanol; dichloromethane; ammonia;

DOI:10.1021/jo00300a021

upstream raw materials:

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

(3,4,5,5-tetramethylcyclopent-2-enyl)methanol

(1S,3R,5R)-3-(hydroxymethyl)-4,4,5-trimethylcyclopentanecarboxylic acid

(1S,3R,5R)-methyl 3-(hydroxymethyl)-4,4,5-trimethylcyclopentanecarboxylate