Acetic Acid → HCID 66748801, compound

HRID 1749155Notes

Reaction equation

HRID 1749155 reaction equation
C[Si](N[Si](C)(C)C)(C)C.C(O)(=O)C.[C:14]1(=O)[CH2:18][CH2:17][CH2:16]C1.[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21]>O>[C:20]([C:22](=[C:16]1[CH2:17][CH2:18][CH2:14]1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 8452CyclopentanoneHCID 13838Hexamethyldisilazane

Product 1

HCID 66748801HCID 66748801, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

HMDS (69.6 g, 0.43 mol) was added dropwise to 350 mL of acetic acid at ambient temp over 5 minutes. Cyclopentanone (20.3 g, 0.29 mol) and ethyl cyanoacetate (65.0 g, 0.57 mol) were added in single portions to the resulting solution. The mixture was stirred at 70° C. overnight after which it was cooled to ambient temperature and the reacting mixture was poured into 600 mL of water, and extracted with ethyl acetate (500 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by flash chromatography (petroleum ether: ethyl acetate=10:1) to give the title compound as a yellow solid (37.0 g, 0.22 mol, 77.2%). LC-MS: m/e=166.2 (M+H+).

Workup

  1. temperaturewas cooled to ambient temperature
  2. extractionextracted with ethyl acetate (500 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford the crude product, which
  7. customwas purified by flash chromatography (petroleum ether: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-25ec0a1516fa4ff48ce72a04419c46c8
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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