Water → Methyl 1-(2-ethynylphenyl)cyclopropanecarboxylate

HRID 592341Notes

Reaction equation

C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1([C:16]([O:18][CH3:19])=[O:17])[CH2:15][CH2:14]1)(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[C:13]1([C:16]([O:18][CH3:19])=[O:17])[CH2:15][CH2:14]1)#[CH:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 1-(2-((trimethylsilyl)ethynyl)phenyl)cyclopropanecarboxylate (I5) (568 mg, 2.09 mmol) in DCM (20.0 mL) at 0° C. was added TBAF (1.0 M in THF, 3.13 mL, 3.13 mmol). The resulting mixture was stirred at 0° C. for 10 minutes then poured into water (50 mL). The aqueous layer was extracted with DCM (2×50 mL), then the combined organic layers were washed with brine, 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, 0-25% EtOAc in petroleum benzine 40-60° C.) to give the title compound K2 as an off-white solid (140 mg, 34%); 1H NMR (400 MHz, d6-DMSO) δ 7.46 (dt, J=7.5, 0.8 Hz, 1H), 7.40-7.25 (m, 3H), 4.32 (s, 1H), 3.52 (s, 3H), 1.54 (q, J=4.1 Hz, 2H), 1.25-1.19 (m, 2H). LCMS-A: rt 5.921 min; m/z 201 [M+H]+.

Workup

extractionThe aqueous layer was extracted with DCM (2×50 mL)
washthe combined organic layers were washed with brine
dry with materialdried over MgSO4
customthe solvent was removed in vacuo
custompurified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-25% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record: ord-21542976f9c44273810d60b4a75c6f3f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238644B2

Reaction notes

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