(2-Bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone → (2-Bromo-3-methylphenyl)(tetrahydrofuran-2-yl)methanone

HRID 1028946Notes

Reaction equation

HRID 1028946 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[O:12][CH2:13][CH2:14][CH:15]=1)=[O:10]>CCOC(C)=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([CH:11]1[CH2:15][CH2:14][CH2:13][O:12]1)=[O:10]

Participants

3

Reactant 1

HCID 67324982(2-Bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone

Product 1

HCID 67325377(2-Bromo-3-methylphenyl)(tetrahydrofuran-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2-bromo-3-methylphenyl)(4,5-dihydrofuran-2-yl)methanone (0.80 g, 2.99 mmol) (mass approximate, based on ˜8 mg/mL Et2O solution) was treated with 500 mL EtOAc and concentrated to ˜100 mL twice. The resulting solution was placed under N2 atmosphere, treated with 5% Pt/C, and then placed under a balloon of H2. Reaction mixture was allowed to stir overnight, then filtered through plug of celite and the filter agent was further washed with 100 mL EtOAc. The solution was concentrated in vacuo and the crude material was absorbed onto a plug of silica gel and purified by column chromatography eluting with a gradient of 20-100% Et2O in hexane to afford (2-bromo-3-methylphenyl)(tetrahydrofuran-2-yl)methanone.

Workup

  1. concentrationconcentrated to ˜100 mL twice
  2. additiontreated with 5% Pt/C
  3. customReaction mixture
  4. filtrationfiltered through plug of celite
  5. washthe filter agent was further washed with 100 mL EtOAc
  6. concentrationThe solution was concentrated in vacuo
  7. customthe crude material was absorbed onto a plug of silica gel
  8. custompurified by column chromatography
  9. washeluting with a gradient of 20-100% Et2O in hexane

Sources & evidence

ORD record
ord-8f067037820e4e65a36b6bf01814f7cf
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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