Tetrahydrofuran → 5-Methyl-3-phenylhexan-2-one

HRID 30367Notes

Reaction equation

HRID 30367 reaction equation
CON(C)[C:4](=[O:16])[CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH:7]([CH3:9])[CH3:8].[CH2:18]1COCC1>C[Mg]Br>[CH3:8][CH:7]([CH3:9])[CH2:6][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4](=[O:16])[CH3:18]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 22270428N-Methoxy-N-methyl-4-methyl-2-phenylpentanamide

Product 1

HCID 131565125-Methyl-3-phenylhexan-2-one

Reagents, catalysts & solvents 1

HCID 178418573HCID 178418573, compoundSolvent

Procedure

To a solution of 75 mg (0.317 mmol) N-methoxy-N-methyl-4-methyl-2-phenylpentanamide in 1 mL dry THF, 0.45 mL 1.4 M methylmagnesium bromide was added. The reaction was stirred for 1 h, quenched with 1.2 N HCl and extracted with EtOAc. The EtOAc solution was washed with brine, dried and concentrated leaving the title compound. 1H NMR: (500 MHz, CDCl3): δ 0.95 (2d, 6H), 1.42 (m, 1H), 1.67 (m, 1H), 1.9 (m, 1H), 2.06 (s, 3H), 3.73 (m, 1H), 7.0-7.4 (m, 5H).

Workup

  1. customquenched with 1.2 N HCl
  2. extractionextracted with EtOAc
  3. washThe EtOAc solution was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-84f7ece9c4e7409582c5649d12d21b03
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Reaction notes

Loading…