Tetrabutylammonium Fluoride → 1-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane

HRID 129321Notes

Reaction equation

HRID 129321 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:22]12[CH2:29][CH2:28][C:25]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[C:35][Si](C)(C)C)([O:26][CH2:27]1)[O:24][CH2:23]2)[CH2:20][CH3:21]>O1CCCC1>[CH2:30]([C:25]12[CH2:28][CH2:29][C:22]([CH2:19][CH2:20][CH3:21])([CH2:23][O:24]1)[CH2:27][O:26]2)[CH2:31][CH2:32][CH2:33][C:34]#[CH:35]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 193733704-n-Propyl-1-(6-trimethylsilylhex-5-ynyl) 2,6-dioxabicyclo[2.2.2]octane

Product 1

HCID 193732891-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride solution (1.0M.,solution 4.0 ml.) was added to a stirred solution of 4-n-propyl-1-(6-trimethylsilylhex-5-ynyl)-2,6-dioxabicyclo[2.2.2]octane in dry tetrahydrofuran (40 ml.) at 20° and the mixture was stirred for 1 hour. The solvent was removed in vacuo and the residue was extracted with diethyl ether and water. The ethereal extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was chromatographed on alumina eluting with dichloromethane: hexane 1:9, saturated with ammonia. 1-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane was obtained as a colourless oil (0.45 g.)

Workup

  1. customThe solvent was removed in vacuo
  2. extractionthe residue was extracted with diethyl ether and water
  3. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on alumina eluting with dichloromethane: hexane 1:9, saturated with ammonia

Sources & evidence

ORD record
ord-337fe4bf49b741dbb429756413bf72c7
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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