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

HRID 2299919Notes

Reaction equation

HRID 2299919 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, 18.3Hz), 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-10ff87ba221c4f77a7a5aa73b285caa3
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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