Potassium ethoxide → HCID 89477712, compound

HRID 1848391Notes

Reaction equation

HRID 1848391 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[C:12](=[O:18])[C:13](OCC)=[O:14])[CH3:2].[O-]CC.[K+]>C1(C)C=CC=CC=1>[OH:14][C:13]1[C:12](=[O:18])[N:7]2[CH:6]([CH2:11][CH2:10][CH2:9][CH2:8]2)[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:19]

Participants

4

Reactant 2

HCID 23670592Potassium ethoxideHCID 89477674HCID 89477674, compound

Product 1

HCID 89477712HCID 89477712, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Intermediate 22B (3.75 g, 13.8 mmol) was suspended in toluene (100 mL) and treated with potassium ethoxide (5.42 mL, 24% in methanol, 13.8 mmol). The clear mixture was heated at 100° C. for 4 h. After cooling to rt, the solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was washed with 10% citric acid twice, brine twice, dried over Na2SO4, filtered and concentrated to afford Intermediate 22C (2.0 g, 64%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.28 (3H, td, J=7.2, 1.8 Hz), 1.46-1.87 (5H, m), 2.19 (1H, br. s.), 3.12-3.51 (1H, m), 4.09-4.23 (2H, m), 4.27-4.42 (2H, m).

Workup

  1. temperatureAfter cooling to rt
  2. customthe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with 10% citric acid twice
  5. dry with materialbrine twice, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5b7667823ec649fd8d800a6a677e431c
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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