Sodium hydride → 5-(t-Butyldimethylsilyloxy)pent-1-yne

HRID 1647771Notes

Reaction equation

HRID 1647771 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[CH2:4][CH2:5][C:6]#[CH:7].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C1COCC1.CCCCCC>[Si:9]([O:8][CH2:3][CH2:4][CH2:5][C:6]#[CH:7])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 793464-Pentyn-1-ol

Product 1

HCID 108673065-(t-Butyldimethylsilyloxy)pent-1-yneYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a suspension of 18.0 g (749 mmol, 1.05 equiv.) of sodium hydride in 500 mL of THF at 0° C. was added a solution of 60.0 g (713 mmol, 1.00 equiv.) of 4-pentyne-1-ol in 150 mL of THF. When the addition was complete the reaction was allowed to warm to room temperature over one hour. To this mixture was added 113 g (749 mmol, 1.05 equiv.) of t-butyldimethylsilyl chloride in 150 mL of THF. The reaction was allowed to stir for 16 hours at room temperature then diluted with 1200 mL of hexane. The organic layer was washed with 500 mL of saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting liquid was distilled at 39°-42° C. at 0.05 mm Hg to yield 135 g (96%) of 1-t-butyldimethylsilyloxy-4-pentyne.

Workup

  1. additionWhen the addition
  2. washThe organic layer was washed with 500 mL of saturated aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. distillationThe resulting liquid was distilled at 39°-42° C. at 0.05 mm Hg

Sources & evidence

ORD record
ord-6197f7e427b141029d5d0c0780d9fc37
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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