3-Phenylfuran → 2,5-Dihydro-2,5-dimethoxy-3-phenylfuran

Participants

Reaction Steps

According to the procedure described in Example 1(a) for the preparation of 3-biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran, 3-phenylfuran (see Pridgen, L. N.; Jones, S. S. J. Org. Chem. 1982, 47, 1590-1592 and Yang, Y.; Wong, H. N. C. Tetrahedron 1994, 32, 9583-9608; 848 mg, 5.89 mmol) provided 1.00 g (82%) of 2,5-dihydro-2,5-dimethoxy-3-phenylfuran as a yellow oil, which was an approximately 80:20 mixture of diastereomers by 1H NMR and used without further purification. 1H NMR (CDCl3): δ 7.64-7.52 (m, 2H), 7.44-7.30 (m, 3H), 6.36-6.30 (m, 0.9H, major+minor isomer), 6.28 (dd, 0.1 H, minor isomer, J=1.2, 3.7 Hz), 6.04-6.00 (m, 0.9H, major+minor isomer), 5.70 (d, 0.8H, major isomer, J=1.2 Hz), 3.52 (s, 2.2H, major isomer), 3.46 (s, 0.60H, minor isomer), 3.43 (s, 2.2H, major isomer), 3.40 (s, 0.60H, minor isomer); Anal. Calculated for C12H14O3•0.04 Br2: C, 67.78; H, 6.64. Found: C, 67.79; H, 6.45.

Provenance & Evidence