Hexamethyldisilazane → HCID 86671849, compound

HRID 573537

Reaction equation

HRID 573537 reaction equation
C[Si](C)(C)[NH:3][Si](C)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:18](=O)[CH2:19][CH3:20])[CH:15]=[CH:16][CH:17]=1.C(#N)[CH:23]([CH2:25][C:26]#[N:27])O>C(O)(=O)C.O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:18](=[C:25]([C:23]#[N:3])[C:26]#[N:27])[CH2:19][CH3:20])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 13838HexamethyldisilazaneHCID 5847653'-MethoxypropiophenoneHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 86671849HCID 86671849, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Hexamethyldisilazane (5.51 mL, 26.3 mmol) was added dropwise to acetic acid (11.30 mL, 197 mmol) at RT under nitrogen. The resulting solution was then added to a solution of 1-[3-(methyloxy)phenyl]-1-propanone (Description 1) (2.7 g, 16.44 mmol) and malonitrile (2.173 g, 32.9 mmol) in acetic acid (10 mL). The reaction mixture was stirred at 70° C. for 12 h. The reaction mixture was cooled to RT then diluted with water (30 mL), the aqueous layer was then extracted with DCM (3×50 mL) and the combined organic extracts were dried over a phase separating column and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, afforded the title compound (3.13 g). LCMS (A) m/z: 211 [M−1]−, Rt 1.40 min (basic).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionthe aqueous layer was then extracted with DCM (3×50 mL)
  3. customthe combined organic extracts were dried over a phase
  4. customseparating column
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel
  7. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-a7acaf093f1344639c977f05a053315f
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Linked notes

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