3-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuran → 4'-(2,5-Dimethoxytetrahydrofuran-3-yl)-biphenyl-4-carbonitrile

HRID 613873Notes

Reaction equation

HRID 613873 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][C:38]([C:41]#[N:42])=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)=[CH:27][CH:26]([O:43][CH3:44])[O:25]1>>[CH3:22][O:23][CH:24]1[CH:28]([C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=3)=[CH:33][CH:34]=2)[CH2:27][CH:26]([O:43][CH3:44])[O:25]1

Participants

3

Reactant 2

HCID 183803263-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuranHCID 183803594'-(2,5-Dimethoxy-2,5-dihydro-furan-3-yl)-biphenyl-4-carbonitrile

Product 1

HCID 183804024'-(2,5-Dimethoxytetrahydrofuran-3-yl)-biphenyl-4-carbonitrileYield 99.3%

Procedure

As described in Example 1(a) for the preparation of 3-biphenyl-4-yl-2,5-dimethoxytetrahydrofuran, 4'-(2,5-dimethoxy-2,5-dihydro-furan-3-yl)-biphenyl-4-carbonitrile (260 mg, 0.846 mmol) was reduced in 2 hours to give 260 mg (99%) of 4'-(2,5-dimethoxytetrahydrofuran-3-yl)-biphenyl-4-carbonitrile as a white solid, mp 149-50° C., which was used without further purification. 1H NMR (CDCl3): δ 7.78-7.26 (m, 8H), 5.30-5.00 (m, 2H), 3.52-3.22 (m, 6H), 2.78-2.00 (m, 3H). IR (KBr): 2910, 2220, 1606, 1498, 1448, 1380, 1224, 1190 cm-1. Anal. Calculated for C19H19NO3.0.3 H2O: C, 72.28; H, 6.28; N, 4.45. Found: C, 72.28; H, 6.19; N, 4.11.

Sources & evidence

ORD record
ord-8ddac06ddc3540228a5d9eb300bc3de5
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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