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

HRID 2308873Notes

Reaction equation

HRID 2308873 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-4fb4852509944540904b64bcaa45e45f
Source dataset
uspto-grants-1987_09
Patent number
US04691027

Reaction notes

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