Tetrabutylammonium Fluoride → 2,6,7-Trioxabicyclo(2.2.2)octane, 4-cyclobutyl-1-(4-ethynylphenyl)-

HRID 1590606Notes

Reaction equation

HRID 1590606 reaction equation
[CH:1]1([C:5]23[CH2:12][O:11][C:8]([C:13]4[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][CH:14]=4)([O:9][CH2:10]2)[O:7][CH2:6]3)[CH2:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:1]1([C:5]23[CH2:6][O:7][C:8]([C:13]4[CH:14]=[CH:15][C:16]([C:19]#[CH:20])=[CH:17][CH:18]=4)([O:11][CH2:12]2)[O:9][CH2:10]3)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 3076492Silane, ((4-(4-cyclobutyl-2,6,7-trioxabicyclo(2.2.2)oct-1-yl)phenyl)ethyl)trimethyl-2×

Product 1

HCID 30764932,6,7-Trioxabicyclo(2.2.2)octane, 4-cyclobutyl-1-(4-ethynylphenyl)-Yield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-cyclobutyl-1-(4-trimethylsilylethynylphenyl)2,6,7-trioxabicyclo[2.2.2]octane (Compound 2) (1.3 g, 3.8 mmol) in dry THF (30 ml) under nitrogen atmosphere was added tetra-butylammonium fluoride (4 ml of 1M solution in THF). The mixture was stirred for one hour, evaporated to dryness and the residue partitioned between water and dichloromethane. The organic layer was separated, dried over anhydrous potassium carbonate and evaporated to leave a residue. Purification on a basic alumina column, eluting with hexane: dichloromethane (9:1 v/v) gave 4-cyclobutyl-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo [2.2.2]octane as a white solid (800 mg, 78%).

Workup

  1. customevaporated to dryness
  2. customthe residue partitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous potassium carbonate
  5. customevaporated
  6. customto leave a residue
  7. customPurification on a basic alumina column
  8. washeluting with hexane: dichloromethane (9:1 v/v)

Sources & evidence

ORD record
ord-63491a481347485fbcc5bcaf84bab7ca
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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