Phosphorus oxychloride → HCID 89524648, compound

HRID 1621007Notes

Reaction equation

HRID 1621007 reaction equation
O[C:2]1([C:8]2([C:12]#[N:13])[CH2:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[O:5]1[CH2:4][CH:3]=[C:2]([C:8]2([C:12]#[N:13])[CH2:11][CH2:10][CH2:9]2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 79130368HCID 79130368, compound

Product 1

HCID 89524648HCID 89524648, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Example 239A (0.4 g, 2.2 mmol) in pyridine (5 mL) was added POCl3 (2 mL, 22 mmol) at room temperature. and the mixture was refluxed overnight. The reaction mixture was cooled to room temperature and carefully quenched with cold water. The resulting mixture was extracted with EtOAc (2×30 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated to obtain a dehydration product 1-(3,6-dihydro-2H-pyran-4-yl)cyclobutanecarbonitrile (0.28 g). This crude material was dissolved in EtOH, followed by the addition of Pd/C. The solution was hydrogenated at room temperature overnight, filtered, and concentrated to obtain the title compound (0.24 g), which was used in the next step without further purification.

Workup

  1. temperatureand the mixture was refluxed overnight
  2. customcarefully quenched with cold water
  3. extractionThe resulting mixture was extracted with EtOAc (2×30 mL)
  4. washThe combined organic phases were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e9d4c4b68fdc4753916f212e440434c3
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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