Acetone → tert-Butyl[(9-iodonon-3-yn-1-yl)oxy]dimethylsilane

HRID 638136Notes

Reaction equation

HRID 638136 reaction equation
[O:1]([CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Cl)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].CC(C)=O.[I-:23].[Na+]>>[O:1]([CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][I:23])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 54000284tert-Butyl[(9-chloronon-3-yn-1-yl)oxy]dimethylsilane

Product 1

HCID 54268398tert-Butyl[(9-iodonon-3-yn-1-yl)oxy]dimethylsilaneYield 96%

Procedure

To 7.9 g (27 mmol) of 17 was added 100 mL of acetone containing 8.2 g (55 mmol) of sodium iodide. The resultant solution was refluxed for 65 hr and then concentrated in vacuo, diluted with water (150 mL) and extracted with ether (3×75 mL). The ether extract was washed with aqueous sodium thiosulfate (2×75 mL) and brine (2×75 mL). Distillation (Vigreux) gave 10.0 g (96% yield) of 18.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water (150 mL)
  3. extractionextracted with ether (3×75 mL)
  4. extractionThe ether extract
  5. washwas washed with aqueous sodium thiosulfate (2×75 mL) and brine (2×75 mL)
  6. distillationDistillation (Vigreux)

Sources & evidence

ORD record
ord-8576265a922148878638e1fe25f99c4f
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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