Acetic Acid → HCID 118274471, compound

HRID 522236Notes

Reaction equation

HRID 522236 reaction equation
O1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)OCC1.[C:12]([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])#[N:13].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1.O>[C:12]([C:14](=[C:5]1[CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH2:10]1)[C:15]([OH:17])=[O:16])#[N:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 70693tert-Butyl cyanoacetateHCID 517165Ammonium AcetateHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 118274471HCID 118274471, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 1,4-dioxaspiro[4.5]decan-8-one (7.00 g, 44.8 mmol), tert-butyl 2-cyanoacetate (6.96 g, 49.3 mmol), ammonium acetate (0.28 g) and acetic acid (1.4 mL) in toluene (90 ml) was refluxed using Dean-Stark water separator to isolate water formed for 48 hours. The reaction mixture was washed twice with water, dried over Na2SO4, filtered, and concentrated in vacuo. To the crude material was added 140 ml of a 2% aqueous sulfuric acid solution and the mixture was refluxed for 1 hour. The reaction mixture was then cooled to room temperature and filtered to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 2.36-2.55 (m, 4H), 3.04 (dd, J=7.6, 5.8 Hz, 2H), 3.30 (d, J=13.6 Hz, 2H).

Workup

  1. customformed for 48 hours
  2. washThe reaction mixture was washed twice with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionTo the crude material was added 140 ml of a 2% aqueous sulfuric acid solution
  7. temperaturethe mixture was refluxed for 1 hour
  8. filtrationfiltered

Sources & evidence

ORD record
ord-baf1e0b17864473a904f4ecc57056551
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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