3-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuran → 2,5-Dimethoxy-3-(4-(pyridin-4-yl)phenyl)tetrahydrofuran

HRID 613881Notes

Reaction equation

HRID 613881 reaction equation
C1(C2C=CC=CC=2)C=CC(C2CC(OC)OC2OC)=CC=1.[CH3:22][O:23][CH:24]1[C:28]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)=[CH:27][CH:26]([O:41][CH3:42])[O:25]1>CO>[CH3:22][O:23][CH:24]1[CH:28]([C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=3)=[CH:33][CH:34]=2)[CH2:27][CH:26]([O:41][CH3:42])[O:25]1

Participants

4

Reactant 2

HCID 183803263-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuranHCID 183803782,5-Dihydro-2,5-dimethoxy-3-(4-(pyridin-4-yl)phenyl)furan

Product 1

HCID 183803222,5-Dimethoxy-3-(4-(pyridin-4-yl)phenyl)tetrahydrofuranYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the procedure described in Example 1(a) for the preparation of 3-biphenyl-4-yl-2,5-dimethoxy-tetrahydrofuran, 2,5-dihydro-2,5-dimethoxy-3-(4-(pyridin-4-yl)phenyl)furan (300 mg, 1.06 mmol) was hydrogenated in MeOH after 6 hours to furnish 300 mg (100%) of 2,5-dimethoxy-3-(4-(pyridin-4-yl)phenyl)tetrahydrofuran as a yellow oil, which was a mixture of diastereomers by NMR, and which was used without further purification. 1H NMR (CDCl3): δ 8.68 (bs, 2H), 7.76-7.36(m, 6H), 5.34-4.94 (m, 2H), 3.72-3.20 (m, 7H), 2.75 (ddd, 0.15H, minor isomer, J=5.9, 10.0, 13.7 Hz), 2.35 (ddd, 0.74H, major isomer, J=5.6, 12.8, 12.8 Hz), 2.20 (dd, 0.0.19H, minor isomer, J=6.9, 12.0 Hz), 2.12 (ddd, 0.16H, minor isomer, J=3.7, 5.9, 13.7 Hz); Anal. Calculated for C17H19NO3.0.2 H2O: C, 70.66; H, 6.77; N, 4.85. Found: C, 70.49; H, 6.74; N, 4.76.

Sources & evidence

ORD record
ord-192c64bdc55545d599d05ea4e78d7bc2
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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