Dimethylformamide dimethyl acetal → HCID 67384334, compound

HRID 1471898Notes

Reaction equation

HRID 1471898 reaction equation
[C:1]1([CH2:7][C:8](=[O:12])[CH2:9][CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>CN(C=O)C>[CH3:15][N:16]([CH3:18])[CH:17]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8](=[O:12])[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 811881-Phenyl-2-pentanone

Product 1

HCID 67384334HCID 67384334, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-phenylpentan-2-one (5.00 g, 30.8 mmol) in dry DMF (80.0 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (6.16 mL, 46.2 mmol). The resulting mixture was heated at 90° C. After 16 h, the reaction mixture was quenched with water, extracted with EtOAc (3×) and washed with brine. The combined organics were dried over MgSO4, filtered, and concentrated to give a yellow oil. This yellow oil was purified by silica gel flash chromatography to give the title compound as a yellow oil (3.51 g). 1H NMR (400 MHz, CDCl3) δ ppm 0.76-0.83 (m, 3H), 0.83-0.89 (m, 2H), 2.11-2.19 (m, 2H), 2.62-2.71 (m, 6H), 7.15-7.42 (m, 5H), 7.61 (s, 1H).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with EtOAc (3×)
  3. washwashed with brine
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customThis yellow oil was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-bbb83ad5446042b482906ea7aab95310
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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