3-Biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran → 3-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuran

HRID 2299915Notes

Reaction equation

HRID 2299915 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:8]([O:14][CH3:15])[O:9][CH:10]([O:12][CH3:13])[CH:11]=2)=[CH:3][CH:2]=1>CCO.CCOC(C)=O.[Pd]>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:2]=[CH:3][C:4]([CH:7]2[CH2:11][CH:10]([O:12][CH3:13])[O:9][CH:8]2[O:14][CH3:15])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 183803523-Biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran

Product 1

HCID 183803263-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuranYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of 3-biphenyl-4-yl-2,5-dihydro-2,5-dimethoxyfuran (1.00 g, 3.55 mmol) and 5% Pd/C (300 mg) in EtOH:EtOAc (1:2) was stirred under H2 atmosphere for 1.75 hours. The catalyst was filtered onto Celite. The filtrate was concentrated to provide 0.97 g (97%) of a diastereomeric mixture of 3-biphenyl-4-yl-2,5-dimethoxy-tetrahydro-furan as a colorless oil which was typically used without purification. 1H NMR: δ 7.60-7.53 (m, 4H), 7.45-7.28 (m, 5H), 5.26 (t, 1H, J=5.5 Hz), 5.02 (d, 1H, J=4.4 Hz), 3.54 (s, 3H), 3.36 (s, 3H), 2.63-2.53 (m, 1H), 2.41-2.30 (m, 1H). Anal. calculated for C18H20O3: C, 76.03; H, 7.09. Found: C, 75.74; H, 6.92.

Workup

  1. filtrationThe catalyst was filtered onto Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-20c682f933f64262bedea161a12d6c19
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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