Diethyl Ether → HCID 24795511, compound

HRID 725172Notes

Reaction equation

HRID 725172 reaction equation
C[Si](C)(C)[O:3][CH2:4][CH2:5][N:6]([CH2:19][CH3:20])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si](C)(C)C)=[CH:9][CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>CO.C1COCC1.C1COCC1>[OH:3][CH2:4][CH2:5][N:6]([CH2:19][CH3:20])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 22119685HCID 22119685, compound

Product 1

HCID 24795511HCID 24795511, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5.0 g, that is 15 mmole of 4-[(2-trimethylsiloxyethyl)ethylamino]trimethylsilylethynylbenzene, prepared in the previous step, dissolved in 60 mL of methanol-THF (1:1) mixture, 33 ml, that is 33 mmole, of 1M tetrabutylammonium fluoride in THF, from Aldrich Chemical Co. was added dropwise. The solution was stirred at room temperature for 1 hour. Ethyl ether was added and the mixture was extracted with water. The organic layer was separated, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was flash column chromatographed on silica gel with 35% ethyl acetate-hexane to produce 2.5 g of a viscous yellow oil at an 88% yield.

Workup

  1. customprepared in the previous step
  2. additionwas added dropwise
  3. extractionthe mixture was extracted with water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customchromatographed on silica gel with 35% ethyl acetate-hexane

Sources & evidence

ORD record
ord-00a5d1d14d374da0ad3eb2cc208fc956
Source dataset
uspto-grants-1998_01
Patent number
US05705570

Reaction notes

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