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

HRID 613845Notes

Reaction equation

[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]([O:14][CH3:15])[O:9][CH:10]([O:12][CH3:13])[CH:11]=2)=[CH:3][CH:2]=1.C1(C2C=COC=2)C=CC=CC=1>>[CH3:15][O:14][CH:8]1[C:7]([C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[CH:11][CH:10]([O:12][CH3:13])[O:9]1

Participants

Reactant 2

HCID 5188023-Phenylfuran

HCID 183803523-Biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran

Product 1

HCID 183803672,5-Dihydro-2,5-dimethoxy-3-phenylfuranYield 82%

Procedure

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 fuirther 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, 0.1H, 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 Cl2H14 03.0.04 Br2 : C, 67.78; H, 6.64. Found: C, 67.79; H, 6.45.

Sources & evidence

ORD record: ord-91b7fb5530ec438fbf215d030a1853d9
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008243

Reaction notes

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