2,3,6,7-Tetrahydro-benzo[1,2-b:4,5-b']difuran Chemical Properties

Melting point:

155 °C

Boiling point:

287.9±40.0 °C(Predicted)

Density 

1.250±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetone, Chloroform, Dichloromethane, Ethyl Acetate

form 

Solid

color 

White

2,3,6,7-Tetrahydro-benzo[1,2-b:4,5-b']difuran Usage And Synthesis

Chemical Properties

White Solid

Uses

2,3,6,7-Tetrahydro-benzo[1,2-b:4,5-b']difuran can be reagent used in the preparation of potent 5-HT2 receptor agonists.

Synthesis

General procedure for the synthesis of 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran from 1,4-dibromo-2,5-bis(2-chloroethoxy)benzene: 10.50 g (26.6 mmol) of 1,4-dibromo-2,5-bis(2-chloroethoxy)benzene was dissolved in 250 mL of anhydrous tetrahydrofuran under the protection of nitrogen and the solution was cooled to 0°C. Using a syringe equipped with a large gauge needle, a 2.5 M hexane solution of n-butyllithium (23.52 mL, 2.2 eq.) was quickly (within 7 seconds) added to the rapidly stirred solution. The reaction mixture was continued to be stirred for 10 minutes before the solvent was removed under vacuum. The residue was partitioned between ethyl acetate and water and the organic phase was dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent was petroleum ether 60-90 °C: ethyl acetate = 20:1) to afford the target product 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (3.47 g, 80% yield) as white crystals. The product was confirmed by NMR hydrogen spectrum (300 MHz, CDCl3): δ 6.63 (2H, s), 4.52 (4H, t, J=8.6 Hz), 3.13 (4H, t, J=8.5 Hz); NMR carbon spectrum (75 MHz, CDCl3): δ 154.12 (C), 125.93 (C), 105.88 (CH). 71.51 (CH2), 30.31 (CH2).

References

[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 2953 - 2961
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 8, p. 1808 - 1814
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 6, p. 1003 - 1010

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