Hydrochloric Acid → HCID 22145935, compound

HRID 554534Notes

Reaction equation

HRID 554534 reaction equation
CCCCCC.C([Li])CCC.C([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br)C1C=CC=CC=1.[CH2:27]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)[CH3:28].Cl>C1COCC1.[OH-].[Pd+2].[OH-].O>[CH2:27]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[OH:19])=[CH:32][CH:31]=1)[CH3:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 248344-EthoxybenzaldehydeHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 22145935HCID 22145935, compoundYield 195%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (2.71 M, 3.8 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (2.5 g, 9.5 mmol) in THF (90 mL) at −78° C. and the mixture solution was stirred at the same temperature for 30 minutes. To this mixture, a solution of 4-ethoxybenzaldehyde (1.29 mL, 1.86 mmol) in THF (30 mL) was added dropwise at −78° C. The reaction mixture was stirred at the same temperature for two hours, and then water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure and the obtained residue was treated by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]. To a methanol solution (26.8 mL) of the obtained crude product, a 20% palladium hydroxide catalyst (147 mg) was added and furthermore 36% HCl (0.4 mL) was added thereto. The mixture was stirred under a hydrogen atmosphere for 24 hours, and then the catalyst was filtered off. The solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (828.1 mg, 38%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for two hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled under reduced pressure
  6. additionthe obtained residue was treated by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]
  7. customTo a methanol solution (26.8 mL) of the obtained crude product
  8. stirringThe mixture was stirred under a hydrogen atmosphere for 24 hours
  9. filtrationthe catalyst was filtered off
  10. distillationThe solvent was distilled under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

Sources & evidence

ORD record
ord-528efe5a10e74ab49fa62a59d0e5e548
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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