Dimethylformamide → 2-Acetoxy-1-(naphth-1-yl)-1-propanone

HRID 33572Notes

Reaction equation

HRID 33572 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[C:16]([O-:19])(=[O:18])[CH3:17].[Na+].CN(C)C=[O:24]>>[C:5]1([CH:3]([O:4][C:16](=[O:18])[CH3:17])[C:2](=[O:24])[CH3:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH3:15][CH:2]([O:19][C:16](=[O:18])[CH3:17])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 2311612-Bromo-1'-propionaphthoneHCID 517045Sodium Acetate

Product 2

HCID 51033133Acetic acid 1-naphthalen-1-yl-2-oxo-propyl esterHCID 597968292-Acetoxy-1-(naphth-1-yl)-1-propanoneYield 49%

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-1-naphthalen-1-yl-propan-1-one (20 g), sodium acetate (7.8 g) and N,N-dimethylformamide (300 mL) was heated at 80° C. for 18 hours. After cooling to room temperature the N,N-dimethylformamide was removed under reduced pressure and the resulting residue was partitioned between dichloromethane (300 mL) and water (300 mL). The organic phase was washed with water (300 mL), brine (300 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford acetic acid 1-naphthalen-1-yl-2-oxo-propyl ester and acetic acid 1-methyl-2-naphthalen-1-yl-2-oxo-ethyl ester (2:1 mixture) (9.0 g, 49%) as a brown oil, 1H NMR (CDCl3): 1.45 (3H, d, J=7.0 Hz), 2.05 (3H, s), 2.15 (3H, s), 2.2 (3H, s), 5.95 (1H, q, J=7.0 Hz), 6.65 (1H, s), 7.45-7.60 (7H, m), 7.85-7.90 (4H, m), 8.0 (1H, d, J=8.1 Hz), 8.1 (1H, d, J=8.3 Hz), 8.35 (1H, d, J=8.6 Hz).

Workup

  1. customwas removed under reduced pressure
  2. customthe resulting residue was partitioned between dichloromethane (300 mL) and water (300 mL)
  3. washThe organic phase was washed with water (300 mL), brine (300 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-00208282f9144c10a73a4b4b26773f68
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Reaction notes

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