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

HRID 613846Notes

Reaction equation

HRID 613846 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 C12H16O3.0.2H2O: 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-a77020b75aeb418683a20fba917166db
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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