2,5-Dihydro-2,5-dimethoxy-3-(4-propylphenyl)-furan → 2,5-Dimethoxy-3-(4-propoylphenyl)-tetrahydrofuran

HRID 613858Notes

Reaction equation

HRID 613858 reaction equation
[CH3:1][O:2][CH:3]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH:5]([O:14][CH3:15])[O:4]1.C[O:17][CH:18]1[C:22](C2C=CC(CCC)=CC=2)=[CH:21]C(OC)O1.COC1C(C2C=CC(CCC)=CC=2)CC(OC)O1>>[CH3:1][O:2][CH:3]1[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([C:18](=[O:17])[CH2:22][CH3:21])=[CH:10][CH:9]=2)[CH2:6][CH:5]([O:14][CH3:15])[O:4]1

Participants

4

Reactant 3

HCID 183803202,5-Dihydro-2,5-dimethoxy-3-(4-propylphenyl)-furanHCID 183803452,5-Dimethoxy-3-(4-propylphenyl)-tetrahydrofuranHCID 185488262,5-Dimethoxy-3-phenyltetrahydrofuran

Product 1

HCID 195932122,5-Dimethoxy-3-(4-propoylphenyl)-tetrahydrofuranYield 100%

Procedure

As described in Example 1(b) for the preparation of 2,5-dimethoxy-3-phenyltetrahydrofuran, 2,5-dihydro-2,5-dimethoxy-3-(4-propylphenyl)-furan (320 mg, 1.29 mmol) was hydrogenated to give 322 mg (100%) of a diastereomeric mixture of 2,5-dimethoxy-3-(4-propylphenyl)-tetrahydrofuran as a viscous colorless oil that was unstable and used immediately without further purification. 1H NMR (CDCl3): δ 7.24 (d, 2H, J=8.1 Hz), 7.12 (d, 2H, J=8.1 Hz), 5.24 (t, 1H, J=5.9 Hz), 3.60-3.30 (m, 6H), 2.59 (d, 1H, J=7.5 Hz), 2.52 (d, 1H, J=8.1 Hz), 2.32 (bs, 3H), 1.62 (q, 2H, J=7.5 Hz), 0.92 (t, 3H, J=7.5 Hz).

Sources & evidence

ORD record
ord-373c263b1e8b475c9573182fd58ead86
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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