Triisopropylsilyl trifluoromethanesulfonate → 1-(Triisopropylsilyl)-1-propyne

HRID 2231268Notes

Reaction equation

HRID 2231268 reaction equation
[C:1]([Li])#[C:2][CH3:3].FC(F)(F)S(O[Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])(=O)=O>CCOCC>[CH3:13][CH:12]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[C:1]#[C:2][CH3:3])[CH3:14]

Participants

4

Reactant 2

HCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 178506788HCID 178506788, compound

Product 1

HCID 40745661-(Triisopropylsilyl)-1-propyneYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Propynyllithium (7.18 g, 156 mmol) was stirred in 160 mL of anhydrous ether at -40° C. under nitrogen and treated dropwise with triisopropylsilyl trifluoromethanesulfonate (47.8 g, 41.93 mL, 156 mmol). The reaction was warmed to room temperature, washed with 2×100 mL of water and 1×100 mL of brine. The organic phase was dried over MgSO4 and concentrated in vacuo. Flash chromatography (95 mm column, petroleum ether eluent, 51/2 inches of silica gel) afforded 25.7 g (84%) of product as a colorless oil.

Workup

  1. washwashed with 2×100 mL of water and 1×100 mL of brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91ac3381b7a14940be802835718a76d2
Source dataset
uspto-grants-1988_11
Patent number
US04782076

Reaction notes

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