Water → Methyl 3-(4-Ethynylphenyl)propanoate

HRID 2042974Notes

Reaction equation

HRID 2042974 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)(C)C.C(=O)([O-])[O-].[K+].[K+].O.CCOC(C)=O>CO>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)#[CH:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 45113001Methyl 3-[4-[(Trimethylsilyl)ethynyl]phenyl]propanoate

Product 1

HCID 25150216Methyl 3-(4-Ethynylphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(4-((trimethylsilyl)ethynyl)phenyl)propanoate (225 mg, 0.86 mmol) and potassium carbonate (234 mg, 1.69 mmol) was dissolved in MeOH (9 mL) and stirred vigorously for 2½ hours at room temperature. The reaction was added water and extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4 before concentrated under vacuum to give 138 mg (90%) of a brown, oily product. Rf: 0.31 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.43-7.40 (m, 2H), 7.17-7.14 (m, 2H), 3.66 (s, 3H), 3.04 (s, 1H), 2.97-2.92 (t, 2H, J=7.7 Hz), 2.65-2.59 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 141.4, 132.3, 128.3, 120.2, 83.5, 76.8, 51.6, 35.3, 30.8; ESI-MS m/z 287.1 (MNa+).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationbefore concentrated under vacuum
  5. customto give 138 mg (90%) of a brown, oily product

Sources & evidence

ORD record
ord-709100815a7147dead651d29ecf45904
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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