Acetic Acid → 1-(2-Ethynylphenyl)cyclopropanecarboxamide

HRID 592352Notes

Reaction equation

HRID 592352 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]([NH2:18])=[O:17])[CH2:15][CH2:14]1)(C)C.C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C(Cl)Cl.O>[C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1([C:16]([NH2:18])=[O:17])[CH2:15][CH2:14]1)#[CH:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 867122751-(2-((Trimethylsilyl)ethynyl)phenyl)cyclopropanecarboxamide

Product 1

HCID 867122761-(2-Ethynylphenyl)cyclopropanecarboxamideYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A cooled (5° C. water/ice bath) solution of 1-(2-((trimethylsilyl)ethynyl)phenyl)cyclopropanecarboxamide (I12) (1.09 g, 4.23 mmol) in DCM (20 mL) containing acetic acid (0.315 mL, 5.50 mmol) was slowly treated with a 1 M solution of TBAF in THF (5.08 mL, 5.08 mmol). The resulting mixture was stirred at room temperature for 2 hours then water (30 mL) was added. The aqueous layer was extracted with DCM (2×15 mL), then the combined organic extracts were washed with water, brine, dried (MgSO4), filtered and evaporated in vacuo to give the title compound as a tan solid (0.780 g, 99%); 1H NMR (300 MHz, CDCl3) δ 7.57 (d, J=6.7 Hz, 1H), 7.31-7.45 (m, 3H), 5.46 (brs, 1H), 5.27 (brs, 1H), 3.38 (s, 1H), 1.75 (dq, J=4.0 Hz, 2H) 1.18 (dq, J=3.7 Hz, 2H). LCMS-B: rt 5.489 min; m/z 186 [M+H]+.

Workup

  1. extractionThe aqueous layer was extracted with DCM (2×15 mL)
  2. washthe combined organic extracts were washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-de8e3fa5a8f8411b8247d5c6be0f8118
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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