ChemicalBook CAS DataBase List 2,5-Diphenylfuran

2,5-Diphenylfuran synthesis

11synthesis methods

Product Name:2,5-Diphenylfuran
CAS Number:955-83-9
Molecular formula:C16H12O
Molecular Weight:220.27

2,5-Diphenylfuran Synthesis: Using the batch general procedure, commercially available trans,trans-1,4-diphenyl-1,3-butadiene (1) (412 mg, 2.00 mmol) and rose Bengal disodium salt (6 mg, 0.005 mmol) in 19:1 CH?Cl?/MeOH (60 mL) provided the intermediate endoperoxide, 3,6-diphenyl-3,6-dihydro-1,2-dioxine (3), as a colorless solid after column chromatography (308 mg, 1.30 mmol, 65%); R_f = 0.15 (9/1 hexanes/ethyl acetate).
1H NMR (CDCl?, 500 MHz): δ 7.77 (d, 4H, J = 8.0 Hz), 7.43 (t, 4H, J = 7.5 Hz), 7.29 (t, 2H, J = 7.5 Hz), 6.75 (s, 2H).
13C {1H} NMR (CDCl?, 126 MHz): δ 137.7, 128.8, 128.7, 128.5, 127.5, 80.3.
Using the general batch procedure and 3 (120 mg, 0.50 mmol), PPh? (144 mg, 0.55 mmol), and CBr? (182 mg, 0.55 mmol), 2,5-Diphenylfuran was obtained as a colorless solid after column chromatography (112 mg, 0.50 mmol, 99%); R_f = 0.40 (9/1 hexanes/ethyl acetate).
1H NMR (CDCl?, 500 MHz): δ 7.77 (d, 4H, J = 7.3 Hz), 7.43 (t, 4H, J = 7.5 Hz), 7.29 (t, 2H, J = 7.5 Hz), 6.76 (s, 2H).
13C {1H} NMR (CDCl?, 126 MHz): δ 153.4, 130.9, 128.8, 127.4, 123.8, 107.3.
IR (ν_max, cm?1): 2980, 1662, 1600, 1587, 1508, 1479, 1447, 1386.

583-05-1
44 suppliers
$39.27/1g

955-83-9
95 suppliers
$65.00/500mg

Yield:955-83-9 94%

Reaction Conditions:

with choline chloride;urea at 80; for 72 h;Paal-Knorr Furan Synthesis;

Steps:

Furan Procedure

General procedure: A solution of dione (1 mmol) in cholinechloride/urea or choline chloride/glycerol (1 mL) was heated to 80 °C andstirred for the designated time. Aftercooling to room temperature, the reaction was diluted with water (2 mL) andextracted with methylene chloride (4 mL).The organic layer was separated, dried, filtered, and concentrated in vacuo to afford the pyrrole productin analytically pure form without further purification.

References:

Handy, Scott;Lavender, Kevin [Tetrahedron Letters,2013,vol. 54,# 33,p. 4377 - 4379] Location in patent:supporting information