Sodium Hydroxide → HCID 131723397, compound

HRID 2228829Notes

Reaction equation

HRID 2228829 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 8900HeptaneSolvent2×

Procedure

The solid cis-3-(3-quinolyl)-2-propen-1-ol (10.0 g, 54.1 mmol), di-tert-butyl dicarbonate (17.6 g, 80.6 mmol, 1.5 equiv), toluene (43 g) and tetra n-butylammonium hydrogen sulfate (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. for 1.5 hours and then 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 pH of the aqueous layers were 10 and 9 respectively. The organic was then washed with an aqueous sodium chloride solution (7 g NaCl, H2O 28 g) before concentration under reduced pressure and a bath temperature of 50° C. The oil which resulted was chased with heptane (2×100 g). The residue was dissolved in 55 mL of heptane to initiate crystallization. This 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. for 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 was then washed with an aqueous sodium chloride solution (7 g NaCl, H2O 28 g) before concentration under reduced pressure and a bath temperature of 50° C
  6. customThe oil which resulted
  7. customcrystallization
  8. customThis product was collected at −5° C.
  9. washwashed with cold heptane (10 mL) and vacuum
  10. customdried at room temperature

Sources & evidence

ORD record
ord-c8235b6998e24d46b2c0602e71094f65
Source dataset
uspto-grants-2002_07
Patent number
US06417366B2

Reaction notes

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