N-Iodosuccinimide → tert-Butyl-{(E)-1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-3-iodo-allyloxy}-dimethylsilane

HRID 406805Notes

Reaction equation

HRID 406805 reaction equation
[C:1]([Si:5]([O:8][CH:9]([CH2:12][CH2:13][C:14]1[S:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[C:15]=1[Cl:23])[C:10]#[CH:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[I:24]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([Si:5]([O:8][CH:9]([CH2:12][CH2:13][C:14]1[S:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[C:15]=1[Cl:23])/[CH:10]=[CH:11]/[I:24])([CH3:6])[CH3:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 21964439tert-Butyl-{1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-prop-2-ynyloxy}-dimethylsilane

Product 1

HCID 21964438tert-Butyl-{(E)-1-[2-(3-chloro-benzo[b]thiophen-2-yl)-ethyl]-3-iodo-allyloxy}-dimethylsilaneYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of alkyne 19 (5.547 g, 15.2 mmol) in dichloromethane (50 mL) was treated with Cp2ZrHCl (5.794 g, 22.5 mmol). The reaction was stirred for 45 min. and then N-iodosuccinimide (4.966 g, 22.1 mmol) was added. After 15 min., saturated sodium bicarbonate solution (200 mL) was added and the mixture was extracted with dichloromethane (2×100 mL). The combined dichloromethane solution was dried (MgSO4), filtered and evaporated. Purification by flash chromatography on silica gel (0-5% ethyl acetate/hexanes) gave 6.608 g (13.1 mmol, 86%) of the vinyl iodide (32).

Workup

  1. waitAfter 15 min.
  2. extractionthe mixture was extracted with dichloromethane (2×100 mL)
  3. dry with materialThe combined dichloromethane solution was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (0-5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ced23174d660498fb013ad7be70b60e0
Source dataset
uspto-grants-2014_06
Patent number
US08754122B2

Reaction notes

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