Ammonium Chloride → (4-Bromo-naphthalen-2-yl)-(5-ethylbenzo[b]-thiophen-2-yl)methanol

HRID 550248Notes

Reaction equation

HRID 550248 reaction equation
CCCCCC.C([Li])CCC.[CH2:12]([C:14]1[CH:22]=[CH:21][C:17]2[S:18][CH:19]=[CH:20][C:16]=2[CH:15]=1)[CH3:13].[Br:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH:34]=[O:35])[CH:25]=1.[Cl-].[NH4+]>C1COCC1>[Br:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([CH:34]([C:19]2[S:18][C:17]3[CH:21]=[CH:22][C:14]([CH2:12][CH3:13])=[CH:15][C:16]=3[CH:20]=2)[OH:35])[CH:25]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 64278735-Ethylbenzo(b)thiopheneHCID 543381284-Bromonaphthalene-2-carbaldehydeHCID 178418244HCID 178418244, compound

Product 1

HCID 67156704(4-Bromo-naphthalen-2-yl)-(5-ethylbenzo[b]-thiophen-2-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 1.44 ml, 2.30 mmol) was added dropwise to a solution of 5-ethylbenzo[b]thiophene (373 mg, 2.30 mmol) in THF (15 ml) at −78° C., and the reaction solution was stirred at the same temperature for 5 minutes. To this mixture, a solution of 4-bromonaphthalene-2-carbaldehyde (515 mg, 2.19 mmol) in THF (5 ml) was added dropwise at −78° C., and the resulting mixture was stirred at the same temperature for two hours and at −20° C. for 30 minutes, and then a saturated ammonium chloride aqueous solution was added 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. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)] to obtain the title compound (780 mg, 90%).

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for two hours and at −20° C. for 30 minutes
  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. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)]

Sources & evidence

ORD record
ord-a319a154b0984f13832477a02b75b6a9
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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