Ethyl Acetate → HCID 59370741, compound

HRID 1873973Notes

Reaction equation

HRID 1873973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([O:11][Si](CC)(CC)CC)[CH2:9]I)=[CH:4][C:3]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C(OCC)(=O)C>C1COCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:9][O:11]2)=[CH:4][C:3]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11078149TBAF tetrahydrofuranHCID 53922285HCID 53922285, compound

Product 1

HCID 59370741HCID 59370741, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(R)—N-(2-Chloro-5-(2-iodo-1-(triethylsilyloxy)ethyl)phenyl)methanesulfonamide (2.2308 g) was dissolved in dehydrated THF (40 mL), and added with 1 mol/L-TBAF-THF solution (10 mL; manufactured by Sigma-Aldrich Co.), followed by replacement with nitrogen and stirring at room temperature for 1 hour. The reaction solution was added to brine, and extraction was carried out once with ethyl acetate. The organic layer was washed once with water and dried over magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=71:29→50:50) to obtain the title compound (0.564 g).

Workup

  1. washThe organic layer was washed once with water
  2. dry with materialdried over magnesium sulfate
  3. customAfter the solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=71:29→50:50)

Sources & evidence

ORD record
ord-1efa9d0800c64757a83c6b6509cb88ce
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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