Ethyl Acetate → HCID 22620175, compound

HRID 1919705Notes

Reaction equation

HRID 1919705 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]([O:10][C:11]2[CH:16]=CC=C[CH:12]=2)=[O:9])[CH:4]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:3]=1.[CH3:23]C(C)([O-])C.[K+].CCOC(C)=O>C1COCC1>[C:11]([O:10][C:8]([N:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:9])([CH3:12])([CH3:16])[CH3:23]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 22620184HCID 22620184, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22620175HCID 22620175, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-42 °C

Procedure

To a stirred solution of 4-Chloro-1-(phenoxycarbonyl)-2-n-hexyl-1,2-dihydropyridine (7.42 g, 23.2 mmol) in 250 ml of THF at −42° C. was added dropwise over 15 minutes a 1.0M solution of potassium t-butoxide (93 mL, 92.87 mmol). The resulting orange solution was stirred for 1 h at −42° C. The cooling bath was removed, and the reaction mixture was allowed to stir for 20 min while being slowly warmed to room temperature. Water (50 ml) and ether (70 ml) were added and the aqueous phase was extracted twice with ether. The combined organic extracts were washed with cold 1.0 N NaOH (2×35 ml), and brine. The organic phase was dried over MgSO4, filtered through Celite, and concentrated in vacuo to give the crude product. Column chromatography with 5% EtOAc in hexanes afforded 5.9 g (81% from previous reaction) as a clear colorless oil that was homogeneous by TLC analysis. 1H NMR (250 MHz) δ 6.85-6.63 (dd, 1H), 5.55 (br s, 1H), 5.23-5.12 (m, 1H), 4.87-4.56 (m, 1H), 1.72-1.25 (m, 19H), 0.89-0.85 (t, 3H).

Workup

  1. customThe cooling bath was removed
  2. stirringto stir for 20 min
  3. temperaturewhile being slowly warmed to room temperature
  4. additionWater (50 ml) and ether (70 ml) were added
  5. extractionthe aqueous phase was extracted twice with ether
  6. washThe combined organic extracts were washed with cold 1.0 N NaOH (2×35 ml), and brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered through Celite
  9. concentrationconcentrated in vacuo
  10. customto give the crude product
  11. custom5.9 g (81% from previous reaction) as a clear colorless oil that

Sources & evidence

ORD record
ord-77d6f34b0c454102b31b1e4b9f374573
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

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