Sodium hydride → 8-Trimethylsilylethynyl-1,4-dioxaspiro[4.5]decane

HRID 727188Notes

Reaction equation

HRID 727188 reaction equation
[H-].[Na+].[CH3:3][Si:4]([C:7]#[CH:8])([CH3:6])[CH3:5].CS(O[CH:14]1[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1)(=O)=O>O1CCCC1>[CH3:3][Si:4]([C:7]#[C:8][CH:14]1[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1)([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66111TrimethylsilylacetyleneHCID 149667411,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Product 1

HCID 197052148-Trimethylsilylethynyl-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a mixture of 3.2 grams (0.08 mole) of sodium hydride (60% in mineral oil) in 25 mL of tetrahydrofuran is stirred, and a solution of 7.9 grams (0.08 mole) of trimethylsilylacetylene in 15 mL of tetrahydrofuran is added dropwise. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about one hour. The reaction mixture is then cooled to 0° C., and a solution of 18.9 grams (0.08 mole) of 8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane in 25 mL of tetrahydrofuran is added dropwise. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature where it is stirred during about 18 hours. After this time the reaction mixture is concentrated under reduced pressure to a residue. The residue is stirred in water, and the mixture is extracted with three 50 mL portions of diethyl ether. The combined extracts are washed with water and dried with magnesium sulfate. The mixture is filtered, and the filtrate is concentrated under reduced pressure, yielding 8-trimethylsilylethynyl-1,4-dioxaspiro[4.5]decane.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture is stirred at ambient temperature for about one hour
  3. additionUpon completion of addition
  4. temperatureto warm to ambient temperature where it
  5. stirringis stirred during about 18 hours
  6. concentrationAfter this time the reaction mixture is concentrated under reduced pressure to a residue
  7. stirringThe residue is stirred in water
  8. extractionthe mixture is extracted with three 50 mL portions of diethyl ether
  9. washThe combined extracts are washed with water
  10. dry with materialdried with magnesium sulfate
  11. filtrationThe mixture is filtered
  12. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-67cdb9211e23479da5ad35178dce4616
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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