Tetrabutylammonium Fluoride → Ethyl 4-ethynyl-3-methylbenzoate

HRID 1259155Notes

Reaction equation

HRID 1259155 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]#[C:14][Si](CC)(CC)CC)[C:5]([O:7][CH2:8][CH3:9])=[O:6].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:13]([C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[CH3:1])#[CH:14]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66874679Ethyl 3-methyl-4-((triethylsilyl)ethynyl)benzoate

Product 1

HCID 86652354Ethyl 4-ethynyl-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3-methyl-4-((triethylsilyl)ethynyl)benzoate (from the previous step) (1.0 eq.) in THF (0.3 M) at 0° C. was added dropwise 1.0 M TBAF in THF (1.2 eq.). After stirring for 10 minutes at 0° C., the reaction was quenched with saturated aqueous sodium bicarbonate solution. The two phases were separated, and the aqueous layer was extracted with ether. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% ethyl acetate in hexane to give ethyl 4-ethynyl-3-methylbenzoate as a white solid.

Workup

  1. customthe reaction was quenched with saturated aqueous sodium bicarbonate solution
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted with ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vaccuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-3f557a10b4734d3a96b1a70aefe2c7e8
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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