Ethyl Acetate → HCID 22620160, compound

HRID 840675Notes

Reaction equation

HRID 840675 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]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]=1.[CH3:22]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[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)=[O:9])([CH3:12])([CH3:16])[CH3:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 22620174HCID 22620174, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22620160HCID 22620160, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-42 °C

Procedure

To a stirred solution of 4-Chloro-1-(phenoxycarbonyl)-2-cyclopentyl-1,2-dihydropyridine (5.52 g, 17.3 mmol) in 200 ml of THF at −42° C. was added dropwise over 15 minutes a 1.0M solution of potassium t-butoxide (50 mL, 50 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 3.71 g (75.7%) of the product which was homogeneous by TLC analysis. 1H NMR (250 MHz) δ6.89-6.67 (dd, 1 H), 5.58 (br s, 1 H), 5.27-5.23 (m, 1 H), 4.92-4.62 (m, 1 H), 2.21 (m, 1 H), 1.892-1.25 (m, 17 H).

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

Sources & evidence

ORD record
ord-a8c616a7988a4954af2063f146474429
Source dataset
uspto-grants-2002_04
Patent number
US06369078B1

Reaction notes

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