ChemicalBook CAS DataBase List [1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester

[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester synthesis

11synthesis methods

Product Name:[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester
CAS Number:54142-64-2
Molecular formula:C31H25F3O6
Molecular Weight:550.52

Dimethyl [2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl]phosphonate

54094-19-8
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[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-4-formylhexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl ester

38754-71-1
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[1,1'-Biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester

54142-64-2
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Yield:54142-64-2 91%

Reaction Conditions:

Stage #1: dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonatewith potassium carbonate in isopropyl alcohol at 25; for 0.5 h;Horner-Wadsworth-Emmons Olefination;
Stage #2: (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate in isopropyl alcohol at 25; for 3 h;Horner-Wadsworth-Emmons Olefination;Reagent/catalyst;Solvent;Temperature;

Steps:

6 Example 6: Manufacture of (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)hexahydro-2Hcyclopenta[b]furan-5-yl biphenyl-4-carboxylate.

Dimethyl 3-(3-(trifluoromethyl) phenoxy) -2-oxopropylphosphonate (0.46 g, 1.43 mmol, 1 eq) was added to a 100 ml 3-neck flask and 10 ml of IPA was added and stirred. K2CO3 (0.6 g, 4.29 mmol, 3 eq) was added at 25 ° C and stirred for 30 minutes. Coriolactone aldehyde (0.5 g, 1.43 mmol, 1 eq) was added and stirred at 25 ° C for 3 hours. The reaction was warmed to 25 ° C and stirred for 2 hours (TLC confirmed completion of the reaction, EA: Hx = 1: 1, rf = 0.65). The reaction was concentrated under reduced pressure (bath 40 ° C). To the reaction were added 10 ml of water and 10 ml of MC and the layers were separated. The water layer was added with 10 ml of MC and extracted one more time. NaCl aqueous solution was added thereto, followed by washing with Na2SO4, followed by filtration and concentration under reduced pressure to obtain a liquid compound.- To obtain 0.61g (yield: 91%). 1 H NMR (400MHz, CDCl3) δ (ppm): 8.04 (d, 2H, HAr), 7.58 (dd, 4H, HAr), 7.43-7.47 (m, 2H, HAr), 7.35-7.40 (m , 2H, HAr), 7.22 (s, 1H, HAr), 7.11 (s, 1H, HAr), 7.01-7.03 (m, 1H, HAr), 6.89 (dd, 1H, CH = CH), 6.56 (d, 1H, CH = CH), 5.33 (q, 1H, CH), 5.10 (t, 1H, CH), 4.72 (s, 2H, CH2), 2.85-2.97 (m, 3H, CH CH2), 2.31-2.65 ( m, 3H, CH2 CH).

References:

KR2016/15100,2016,A Location in patent:Paragraph 0096-0100

31752-99-5 Synthesis