Ethyl Acetate → HCID 89525845, compound

HRID 1621013Notes

Reaction equation

HRID 1621013 reaction equation
[C:1]([C:3]1([C:7]2(O)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:6][CH2:5][CH2:4]1)#[N:2].O=P(Cl)(Cl)Cl.C(OCC)(=O)C>N1C=CC=CC=1>[C:1]([C:3]1([C:7]2[CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 86685238HCID 86685238, compound

Product 1

HCID 89525845HCID 89525845, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 265A (2.4 g, 9 mmol) in pyridine (50 mL) was added POCl3 (8.4 mL, 90 mmol) dropwise and the solution was stirred at 60° C. for 12 hours. Pyridine was removed under reduced pressure and the solution was basified with 1 N NaOH. The aqueous layer was extracted with EtOAc (25 mL×3). The combined organic phases were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography eluted with petroleum ether:ethyl acetate=20:1 to obtain the title compound (2.6 g, 44.3% yield) as a colorless oil. 1H NMR: (400 MHz, CDCl3): δ 5.80 (d, J=9.6 Hz, 1H), 4.26-4.17 (m, 4H), 2.66-2.59 (m, 2H), 2.45-2.38 (m, 2H), 2.34-2.24 (m, 1H), 2.10-2.00 (m, 1H), 1.49 (s, 9H).

Workup

  1. customPyridine was removed under reduced pressure
  2. extractionThe aqueous layer was extracted with EtOAc (25 mL×3)
  3. washThe combined organic phases were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography
  8. washeluted with petroleum ether

Sources & evidence

ORD record
ord-14f21f3a87f94674b548577a2ff30bc4
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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