Water → 2-(2-Ethynylphenyl)butanamide

HRID 592338Notes

Reaction equation

C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([CH2:17][CH3:18])[C:14]([NH2:16])=[O:15])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C(Cl)Cl>[C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([CH2:17][CH3:18])[C:14]([NH2:16])=[O:15])#[CH:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(2-((trimethylsilyl)ethynyl)phenyl)butanamide (I3) (149 mg, 0.574 mmol) in DCM (10.0 mL) at 0° C. under nitrogen was added TBAF (1.0 M in THF, 0.86 mL, 0.86 mmol). The resulting mixture was stirred at 0° C. for 5 minutes then poured into water (50 mL). The organic phase was separated and the aqueous layer was extracted with DCM (2×40 mL). The combined organic layers were washed with brine (40 mL), dried over MgSO4 and the solvent was removed in vacuo. The residue was adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-75% EtOAc in petroleum benzine 40-60° C.) to give the title compound K1 as an off-white solid (104 mg, 97%); 1H NMR (400 MHz, d6-DMSO) δ 7.50-7.43 (m, 2H), 7.35 (td, J=7.7, 1.5 Hz, 1H), 7.31 (s, 1H), 7.23 (td, J=7.5, 1.3 Hz, 1H), 6.93 (s, 1H), 4.37 (s, 1H), 3.85 (dd, J=8.6, 6.4 Hz, 1H), 1.97-1.83 (m, 1H), 1.61 (J m, 1H), 0.84 (t, J=7.3 Hz, 3H). LCMS-A: rt 5.265 min; m/z 188 [M+H]+.

Workup

customThe organic phase was separated
extractionthe aqueous layer was extracted with DCM (2×40 mL)
washThe combined organic layers were washed with brine (40 mL)
dry with materialdried over MgSO4
customthe solvent was removed in vacuo
custompurified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-75% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record: ord-cc71fbd4fc8843439b4d90434dc9b0b5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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