Sodium Hydroxide → HCID 131723397, compound

HRID 2304769Notes

Reaction equation

HRID 2304769 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](/[CH:11]=[CH:12]\[CH2:13][OH:14])[CH:2]=1.[C:15]([O:22]C(OC(C)(C)C)=O)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O.CCCCCCC>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](/[CH:11]=[CH:12]\[CH2:13][OH:14])[CH:2]=1.[C:18]([O:17][C:15](=[O:16])[O-:22])([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 59900821HCID 59900821, compound

Product 1

HCID 131723397HCID 131723397, compoundYield 88.3%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8900HeptaneSolvent

Procedure

The solid cis-3-(3-quinolyl)-2-propen-1-ol (10.0 g, 54.1 mmol), di-t-butyl dicarbonate (17.6 g, 80.6 mmol, 1.5 equiv), toluene (43 g) and tetra-n-butylammonium hydrogensulfate (0.68 g, 2.0 mmol) were combined and stirred (mechanically) in a three-necked round-bottom flask. To this stirring mixture was slowly added an aqueous sodium hydroxide solution (28 g H2O and 7.0 g, NaOH) over 10 minutes. The temperature of the biphasic mixture warmed from 18° C. to 31° C. over 1.5 hours and was allowed to stir overnight at room temperature. The reaction was then diluted with toluene (33 mL) and water (19 mL). The layers were separated (aq. pH 12) and the organic was washed consecutively with water (1×28 mL) and 5% aq. NaCl (1×28 mL). The organic layer was then washed with an aqueous sodium chloride solution (7 g NaCl, 28 g H2O) before concentration under reduced pressure and a bath temperature of 50° C. The oil which resulted was dissolved in heptane (100 g) and concentrated by rotary evaporation (2×). The resulting residue was dissolved in 55 mL of heptane for crystallization. The product was collected at −5° C., washed with cold heptane (10 mL) and vacuum dried at room temperature to provide a white to off-white colored solid (13.6 g, 88.3%). Purity as determined by HPLC was 98.7%.

Workup

  1. temperatureThe temperature of the biphasic mixture warmed from 18° C. to 31° C. over 1.5 hours
  2. stirringto stir overnight at room temperature
  3. customThe layers were separated (aq. pH 12)
  4. washthe organic was washed consecutively with water (1×28 mL) and 5% aq. NaCl (1×28 mL)
  5. washThe organic layer was then washed with an aqueous sodium chloride solution (7 g NaCl, 28 g H2O) before concentration under reduced pressure and a bath temperature of 50° C
  6. customThe oil which resulted
  7. concentrationconcentrated by rotary evaporation (2×)
  8. dissolutionThe resulting residue was dissolved in 55 mL of heptane for crystallization
  9. customThe product was collected at −5° C.
  10. washwashed with cold heptane (10 mL) and vacuum
  11. customdried at room temperature

Sources & evidence

ORD record
ord-434db4eabb1047c795d896b42a76ce23
Source dataset
uspto-grants-2002_08
Patent number
US06437106B1

Reaction notes

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