ChemicalBook CAS DataBase List (+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE

(+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE synthesis

7synthesis methods

Product Name:(+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE
CAS Number:53872-60-9
Molecular formula:C18H19F3O5
Molecular Weight:372.34

114488-91-4 Synthesis

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

114488-91-4
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(+)-(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(1E,3R)-3-HYDROXY-4-(3-TRIFLUOROMETHYL)PHENOXY-1-BUTENYL]-2H-CYCLOPENTA[B]FURAN-2-ONE

53872-60-9
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Yield:53872-60-9 83.66%

Reaction Conditions:

with potassium carbonate in methanol at 25; for 1 h;

Steps:

2.5 Step 5: Synthesis of the compound of formula IV {(3aR, 4R, 5R, 6aS) -5-hydroxy-4 - ((R, E) -3-hydroxy-4- (3- (trifluoromethyl) phenoxy ) But-1-enyl) hexahydro-2H-cyclopenta [b] furan-2-one}
To a solution of the compound of formula III (5.95 g, 12.488 mmol, 1 eq) prepared in step 4 in 60 ml of MeOH Dissolved and K2CO3 (2.24 g, 16.234 mmol, 1.3 eq) was added to the reaction mixture while stirring at 25 DEG C, followed by stirring. The reaction was stirred at 1 hour; After stirring for 1 hour, the reaction was terminated. The reaction solution After cooling to 0 ° C, the pH was adjusted to 2 with 20 mL of 2N HCl. The crystals were removed by filtration, and the filtrate was concentrated under reduced pressure. The concentrate was separated by adding 60 mL of methylene chloride and 60 mL of water, and the organic layer was washed with 60 mL of brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The brown oil was collected by column chromatography with ethyl acetate: hexane = 2: 1 to obtain a yellow oil (3.89 g, 83.66%).

References:

MIRAE FINE CHEMICAL CO LTD[KR];Jeong, Jin Hyun;Sim, Yoo Lan;Yang, Woo Lam;Hwang, Sung Kwan;Park, Jang Ha;Choe, Seon Hee KR2017/25682, 2017, A Location in patent:Paragraph 0136; 0158-0160

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54142-64-2 Synthesis