Tetrabutylammonium Fluoride → Methyl 3-ethynyl-4-methylbenzoate

HRID 570976Notes

Reaction equation

HRID 570976 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]#[C:13][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:12]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[CH3:1])[C:6]([O:8][CH3:9])=[O:7])#[CH:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70557105Methyl 4-methyl-3-((trimethylsilyl)ethynyl)benzoate

Product 1

HCID 53403239Methyl 3-ethynyl-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of methyl 4-methyl-3-[(trimethylsilyl)ethynyl]benzoate (2.3 g) in THF (40 ml) was added tetrabutylammonium fluoride (1.0M in THF, 3.2 ml, 11 mmol) at ambient temperature and stirred for 15 minutes, concentrated and the residue purified by flash chromatography on silica gel (elution with 2% ethyl acetate in n-hexane) to provide methyl 3-ethynyl-4-methylbenzoate.

Workup

  1. concentrationconcentrated
  2. customthe residue purified by flash chromatography on silica gel (elution with 2% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-1230c1c639434298ad51783ae8a0e624
Source dataset
uspto-grants-2015_05
Patent number
US09024021B2

Reaction notes

Loading…