N-Iodosuccinimide → HCID 131736288, compound

HRID 1053796Notes

Reaction equation

HRID 1053796 reaction equation
[C:1]([Si:5]([O:8][CH:9]([C:21]#[CH:22])[CH2:10][C:11]1[S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]=1[Cl:20])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[I:23]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([Si:5]([O:8][CH:9](/[CH:21]=[CH:22]/[I:23])[CH2:10][C:11]1[S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]=1[Cl:20])([CH3:6])[CH3:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 131736289HCID 131736289, compound

Product 1

HCID 131736288HCID 131736288, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cp2ZrHCl (628 mg, 2.5 mmol) was added to a solution of tert-butyl((1-(3-chlorobenzo[b]thiophen-2-yl)but-3-yn-2-yl)oxy)dimethylsilane (565 mg, 1.61 mmol) in CH2Cl2 (11 mL). The reaction was stirred for 1 h and then N-iodosuccinimide (585 mg, 2.6 mmol) was added. After 30 minutes, 30 mL saturated NaHCO3 solution was added and the resulting mixture was extracted with CH2Cl2 (3×30 mL). The combined organic solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (669 mg, 87%).

Workup

  1. waitAfter 30 minutes
  2. extractionthe resulting mixture was extracted with CH2Cl2 (3×30 mL)
  3. dry with materialThe combined organic solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ef78afd533b247dea524dad3346cce35
Source dataset
uspto-grants-2016_07
Patent number
US09394273B2

Reaction notes

Loading…