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

HRID 382129Notes

Reaction equation

HRID 382129 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-biphenyl4-yl-2,5-dimethoxy-tetrahydro-furan as a colorless oil which was typically used without purification.

Workup

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

Sources & evidence

ORD record
ord-084a61bc1d054a3aa318f92bcfe9a8fc
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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