Sodium Hydroxide → 3-(3-Quinolyl)-2-propen-1-ol t-butyl carbonate

HRID 2304768Notes

Reaction equation

HRID 2304768 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.C(Cl)Cl>[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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 539384493-(3-Quinolyl)-2-propen-1-ol

Product 1

HCID 865842593-(3-Quinolyl)-2-propen-1-ol t-butyl carbonate

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 500-mL three-necked round-bottom flask equipped with an overhead mechanical stirrer was charged 3-(3-quinolyl)-2-propen-1-ol (13.03 g, 70.43 mmol) as a mixture of cis and trans isomers (81% cis, and 19% trans), di-t-butyl dicarbonate (16.91 g, 77.48 mmol, 1.11 equiv), tetra n-butyl ammonium hydrogensulfate (742 mg, 2.17 mmol) and methylene chloride (135 mL). The stirred mixture was cooled to 0 to 5° C. at which time aqueous 25% sodium hydroxide (33.3 mL) was added over 45 minutes such that the internal temperature did not rise above 20° C. Upon completion of the reaction (1 to 4 hours), the reaction mixture was diluted with methylene chloride (50 mL) and washed with water (2×125 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide the 3-(3-quinolyl)-2-propen-1-ol t-butyl carbonate: 18.35 g (91.4%) as an oil. This material can be further purified by chromatography on silica gel to provide purified carbonate as a colorless oil which retains the original ratio of cis and trans isomers: 17.50 g, 87.2%.

Workup

  1. customTo a 500-mL three-necked round-bottom flask equipped with an overhead mechanical stirrer
  2. additionwas added over 45 minutes such that the internal temperature
  3. customdid not rise above 20° C
  4. customUpon completion of the reaction (1 to 4 hours)
  5. washwashed with water (2×125 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f792e6cf2cd944e79c2c521928d1f5e7
Source dataset
uspto-grants-2002_08
Patent number
US06437106B1

Reaction notes

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