Reaction #1365712

Reaction equation

silane

2-methyl-3-buten-2-ol

trimethylsilane

→

product

2-methyl-4-trimethylsilyl-2-butanol

Solvents

toluene

Conditions

Workup

1. 1
   OtherA 250 mL 3-neck round-bottom flask was equipped with a magnetic stirrer, dry-ice condenser with a nitrogen bubbler
2. 2
   Temperaturecooled to below 10° C
3. 3
   workup.ADDITIONwas added slowly over 3 hours
4. 4
   OtherThe ice-water cooling bath was removed
5. 5
   Temperaturethe dry-ice condenser was maintained with dry-ice
6. 6
   OtherThe condenser was removed
7. 7
   workup.DISTILLATIONthe reaction mixture distilled under vacuum
8. 8
   workup.DISTILLATIONThe major fraction distilling at 105-108° C. at 200 milliTorr
9. 9
   Otherwas collected

Procedure

A 250 mL 3-neck round-bottom flask was equipped with a magnetic stirrer, dry-ice condenser with a nitrogen bubbler, thermocouple thermometer, ice water cooling bath, and a gas inlet tube attached through a back flow trap to a cylinder of trimethylsilane. The flask was charged with 68.9 g (0.80 mol) of 2-methyl-3-buten-2-ol and 600 mg of platinum-divinyl tetramethyl disiloxane complex in toluene (about 2 mol % platinum) and cooled to below 10° C. The reaction temperature was maintained between 5 and 10° C. as the silane (63 grams, 0.85 mol) was added slowly over 3 hours. The ice-water cooling bath was removed but the dry-ice condenser was maintained with dry-ice while stirring overnight. The condenser was removed and replaced with a distillation apparatus and the reaction mixture distilled under vacuum. The major fraction distilling at 105-108° C. at 200 milliTorr was collected, yielding 124 grams of product.

Source