2,5-Dihydro-2,5-dimethoxy-3-phenylfuran → 2,5-Dimethoxy-3-phenyltetrahydrofuran

HRID 566740Notes

Reaction equation

HRID 566740 reaction equation
[CH3:1][O:2][CH:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]([O:14][CH3:15])[O:4]1>CCOC(C)=O.[Rh]>[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

Participants

4

Reactant 1

HCID 183803672,5-Dihydro-2,5-dimethoxy-3-phenylfuran

Product 1

HCID 185488262,5-Dimethoxy-3-phenyltetrahydrofuranYield 98%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,5-dihydro-2,5-dimethoxy-3-phenylfuran (590 mg, 2.86 mmol) and 10% Rh/Al2O3 (110 mg) in EtOAc (10 mL) was stirred under H2 atmosphere for 24 hours. The catalyst was filtered onto Celite and rinsed with EtOAc. The filtrate was concentrated in vacuo to afford 583 mg (98%) of 2,5-dimethoxy-3-phenyl-tetrahydrofuran as a colorless oil which was typically used without further purification. 1H NMR: δ 7.40-7.18 (m, 5H), 5.30-4.80 (m, 2H), 3.70-3.40 (m, 6H), 2.78-2.43 (m, 1.2H), 2.34 (ddd, 0.75H, J=5.6, 12.7, 18.3 Hz), 2.17 (dd, 0.1H, J=8.4, 12.8 Hz). Anal. Calcd for C12H16O3•0.2 H2O: C, 68.03; H, 7.80. Found: C, 68.11; H, 7.60.

Workup

  1. filtrationThe catalyst was filtered onto Celite
  2. washrinsed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9ce5b220175643b39e74666e3193f733
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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