Malononitrile → HCID 86671850, compound

HRID 573552Notes

Reaction equation

HRID 573552 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[CH3:10][CH:11]([CH3:23])[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=O.[C:24](#[N:28])[CH2:25][C:26]#[N:27]>C(O)(=O)C>[CH3:10][CH:11]([CH3:23])[CH2:12][C:13](=[C:25]([C:24]#[N:28])[C:26]#[N:27])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 13838HexamethyldisilazaneHCID 18728272HCID 18728272, compound

Product 1

HCID 86671850HCID 86671850, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of acetic acid (14.36 mL, 251 mmol), was added hexamethyldisilazane (7.01 mL, 33.5 mmol) dropwise. The resulting solution was added to a solution of 3-methyl-1-[3-(methyloxy)phenyl]-1-butanone (4.02 g, 20.91 mmol) (Description 18) and malononitrile (2.76 g, 41.8 mmol) in acetic acid (15 mL). The mixture was stirred for 7 h at 70° C. The solution was cooled to RT and partitioned between toluene (167 mL) and water (130 mL). The aqueous layer was further extracted with toluene (70 mL). The combined organic layers were concentrated, and purified by chromatography on silica gel, eluting with DCM, to afford the title compound (4.42 g). LCMS (B) m/z: 241 [M+1]+, Rt 3.14 min.

Workup

  1. temperatureThe solution was cooled to RT
  2. custompartitioned between toluene (167 mL) and water (130 mL)
  3. extractionThe aqueous layer was further extracted with toluene (70 mL)
  4. concentrationThe combined organic layers were concentrated
  5. custompurified by chromatography on silica gel
  6. washeluting with DCM

Sources & evidence

ORD record
ord-ba6115266aeb4119b36bc8c482e283a1
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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