Sodium Hydroxide → HCID 22630148, compound

HRID 2307096Notes

Reaction equation

HRID 2307096 reaction equation
[C:1]([C:3]([C:12]1([CH3:22])[CH2:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:14]([CH3:21])([CH3:20])[CH2:13]1)([CH2:9][CH:10]=[CH2:11])C(OCC)=O)#[N:2].[Cl-:23].[Li+].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CS(C)=O.C(OCC)C.O>[ClH:23].[CH3:22][C:12]1([CH:3]([CH2:9][CH:10]=[CH2:11])[CH2:1][NH2:2])[CH2:17][C:16]([CH3:18])([CH3:19])[CH2:15][C:14]([CH3:20])([CH3:21])[CH2:13]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22630117HCID 22630117, compound

Product 1

HCID 22630148HCID 22630148, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
177.5 °C

Procedure

To a solution of ester 48 (0.9 g, 2.95 mmol) in DMSO (10 ml) was added water (0.53 ml, 2.95 mmol) and lithium chloride (0.25 g, 5.9 mmol). The mixture was stirred for 3 h at 175-180° C., then it was cooled and water (30 ml) was added. The mixture was extracted with diethyl ether. The extract was washed with water and with brine, dried over anhydrous MgSO4, filtered and concentrated to 10 ml volume. The solution obtained was added dropwise to a suspension of lithium aluminum hydride (0.25 g, 6.6 mmol) in diethyl ether (15 ml) and stirred at reflux for 3 h. The mixture was cooled and treated with 20% aqueous NaOH, and extracted with diethyl ether. The extract was washed with brine, dried over NaOH, filtered and treated with anhydrous HCl solution in diethyl ether. After evaporation of the solvent, the residue was purified by chromatography on silica gel (chloroform-methanol, 20:1) to give 49 (0.245 g, 31%) as a colorless solid. 1H NMR (DMSO-D6, TMS): 0.92, 0,96 and 1.04 (total 15H, all s, 3′,5′-CH3 and 1′-CH3), 1.00-1.65 (total 6H, m, ring-CH2); 1.85-2.40 (3H, m, 3-CH2, 4-CH); 2.60-3.10 (2H, m, CH2N); 4.90-5.25 (2H, m, ═CH2); 5.62-6.10 (1H, m, ═CH) and 7.92 ppm (3H, br s, NH3+).

Workup

  1. temperatureit was cooled
  2. extractionThe mixture was extracted with diethyl ether
  3. washThe extract was washed with water and with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to 10 ml volume
  7. customThe solution obtained
  8. stirringstirred
  9. temperatureat reflux for 3 h
  10. temperatureThe mixture was cooled
  11. extractionextracted with diethyl ether
  12. washThe extract was washed with brine
  13. dry with materialdried over NaOH
  14. filtrationfiltered
  15. additiontreated with anhydrous HCl solution in diethyl ether
  16. customAfter evaporation of the solvent
  17. customthe residue was purified by chromatography on silica gel (chloroform-methanol, 20:1)

Sources & evidence

ORD record
ord-d77963aa40584ae29be0ca20f56001cc
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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