Ethyl Acetate → 2-(4-Ethynyl-2-methylphenoxy)ethanol

HRID 734788Notes

Reaction equation

HRID 734788 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][C:20]1[CH:29]=[C:28]([C:30]#[C:31][Si](C)(C)C)[CH:27]=[CH:26][C:21]=1[O:22][CH2:23][CH2:24][OH:25].CCOC(C)=O>C1COCC1>[C:30]([C:28]1[CH:27]=[CH:26][C:21]([O:22][CH2:23][CH2:24][OH:25])=[C:20]([CH3:19])[CH:29]=1)#[CH:31]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 690546062-(2-Methyl-4-trimethylsilanylethynylphenoxy)ethanol

Product 1

HCID 575658612-(4-Ethynyl-2-methylphenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.8 g (74.4 mmol) of TBAF was added at RT to a solution of 16.8 g (67.6 mmol) of 2-(2-methyl-4-trimethylsilanylethynylphenoxy)ethanol in 500 mL of THF and the mixture was stirred for 3 hours at RT. The reaction mixture was evaporated down in vacuo and the residue dissolved in EtOAc. The organic phase was washed with water and saturated aqueous NaCl solution, dried over sodium sulfate, and evaporated down in vacuo. The crude product was used in the next reaction step without further purification. Yield: 12.0 g (quant. yield); C11H12O2 (M=176.212); calc.: molpeak (M)+: 176; found: molpeak (M)+: 176; Rf value: 0.24 (silica gel, cyc/EtOAc 2:1).

Workup

  1. customThe reaction mixture was evaporated down in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic phase was washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated down in vacuo
  6. customThe crude product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-282c171ba39d4cc6b48268fd8384ae65
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

Loading…