Potassium Carbonate → 4-tert-Butyl-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile

HRID 2165870Notes

Reaction equation

HRID 2165870 reaction equation
[C:1]([C:5]12[CH2:12][O:11][C:8]([C:13]3[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][CH:14]=3)([O:9][CH2:10]1)[O:7][CH:6]2[C:25]#[N:26])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([C:5]12[CH2:12][O:11][C:8]([C:13]3[CH:14]=[CH:15][C:16]([C:19]#[CH:20])=[CH:17][CH:18]=3)([O:9][CH2:10]1)[O:7][CH:6]2[C:25]#[N:26])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14064600HCID 14064600, compound

Product 1

HCID 1838894-tert-Butyl-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2.2.2]octane-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-t-butyl-3-cyano-1-[4-(2-trimethylsilylethynyl)-phenyl]-2,6,7-trioxabicyclo[2,2,2]octane (1.3 g.) and anhydrous potassium carbonate in dry methanol (125 ml.) was stirred under dry nitrogen for 2 hours. The resulting solution was evaporated in vacuo. The residue was taken up in diethyl ether and the ethereal solution was washed with water. The ethereal solution was dried over anhydrous sodium sulphate and evaporated in vacuo. The residue was purified by chromatography on alumina eluting with hexane:dichloromethane 4:1, saturated with ammonia. 4-t-butyl-3-cyano-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2,2,2]octane was obtained as pale yellow needles (600 mg.).

Workup

  1. customThe resulting solution was evaporated in vacuo
  2. washthe ethereal solution was washed with water
  3. dry with materialThe ethereal solution was dried over anhydrous sodium sulphate
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on alumina eluting with hexane:dichloromethane 4:1, saturated with ammonia

Sources & evidence

ORD record
ord-c15358f83ba14f39bc8b3dfa82935e1c
Source dataset
uspto-grants-1990_07
Patent number
US04942173

Reaction notes

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