Hydrochloric Acid → HCID 12110025, compound

HRID 1057895Notes

Reaction equation

HRID 1057895 reaction equation
Br[C:2]1[CH:14]=[C:13]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[C:5]2[CH2:6][C:7]3([O:12][C:4]=2[C:3]=1[O:23][CH3:24])[CH2:11][CH2:10][CH2:9][CH2:8]3.C([Li])CCC.Cl.O>C1COCC1.CCCCCC>[CH3:24][O:23][C:3]1[C:4]2[O:12][C:7]3([CH2:11][CH2:10][CH2:9][CH2:8]3)[CH2:6][C:5]=2[C:13]([C:15]#[C:16][C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)=[CH:14][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 22734272HCID 22734272, compoundHCID 178418339Butyllithium

Product 1

HCID 12110025HCID 12110025, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under an argon atmosphere, a solution (2.6 ml) of Compound 142b (0.1 g) obtained in Step B in THF was cooled to −78° C., and then a 1.7M solution (0.2 ml) of n-butyl lithium in hexane was dropwise added thereto, followed by stirring at the same temperature for one hour. The reaction solution was adjusted to pH 7 by adding dropwise 1N hydrochloric acid, followed by stirring at room temperature for one hour. A small amount of water was added to the reaction solution and the mixture was extracted with ether. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2) to give Compound 142 (0.014 g, 17.4%) as pale-yellow crystals.

Workup

  1. stirringby stirring at room temperature for one hour
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-fb4437998b574612a7c75e69efee6614
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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