Methyl 4-trimethylsilylethynylbenzoate → Methyl 4-ethynylbenzoate

HRID 527751

Reaction equation

HRID 527751 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:6]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 640161Methyl 4-trimethylsilylethynylbenzoateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 640163Methyl 4-ethynylbenzoateYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((trimethylsilyl)ethynyl)benzoate (1.35 g, 5.35 mmol) in THF (10 mL) was added TBAF (1 M solution in THF, 10.7 mL, 10.70 mmol). The resulting brown reaction mixture was stirred at rt for 3 h and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 5% EtOAc/hexane) to afford the title compound as a white solid (0.65 g, 76%). 1H NMR (CDCl3) δ 8.00 (d, J=8.6 Hz, 2H), 7.56 (d, J=8.6 Hz, 2H), 3.93 (s, 3H), 3.23 (s, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography (eluting with 5% EtOAc/hexane)

Sources & evidence

ORD record
ord-47111b569f9f4343b680312b67ded67b
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Linked notes

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