Sodium Iodide → 5-t-Butyldimethylsilyloxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2350995Notes

Reaction equation

HRID 2350995 reaction equation
[Si:1]([O:8][C:9]1[C:10]([CH3:24])=[C:11]([CH3:23])[C:12]2[O:16][CH:15]([CH2:17][CH2:18][CH2:19]Cl)[S:14][C:13]=2[C:21]=1[CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I-:25].[Na+]>CC(C)=O>[Si:1]([O:8][C:9]1[C:10]([CH3:24])=[C:11]([CH3:23])[C:12]2[O:16][CH:15]([CH2:17][CH2:18][CH2:19][I:25])[S:14][C:13]=2[C:21]=1[CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 148021845-t-Butyldimethylsilyloxy-2-(3-chloropropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Product 1

HCID 148021855-t-Butyldimethylsilyloxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.06 g of 5-t-butyldimethylsilyloxy-2-(3-chloropropyl)-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 78), 4.1 g of sodium iodide and 40 ml of acetone was heated under reflux for 10 hours. The reaction product was then cooled, after which it was treated in the same manner as described in (a) above, to give the title compound having the same Rf value, infrared absorption spectrum and mass spectrum as the product of (a) above.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureThe reaction product was then cooled
  4. additionafter which it was treated in the same manner

Sources & evidence

ORD record
ord-31567dcece63403eb5e01c3dd8f4c9bf
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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