Trimethylsilylacetylene → Methyl 3-[4-[(Trimethylsilyl)ethynyl]phenyl]propanoate

HRID 2042973Notes

Reaction equation

HRID 2042973 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16]>>[CH3:14][Si:15]([C:18]#[C:19][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1)([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 554150Methyl 3-(4-iodophenyl)propanoate

Product 1

HCID 45113001Methyl 3-[4-[(Trimethylsilyl)ethynyl]phenyl]propanoate

Procedure

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (250 mg, 0.86 mmol) and trimethylsilylacetylene (0.22 mL, 1.70 mmol) according to the general procedure IA. After filtration through Celite, the product was obtained as a brown oil and used without purification in the next step. Rf: 0.38 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.39-7.37 (m, 2H), 7.13-7.11 (m, 2H), 3.65 (s, 3H), 2.96-2.91 (t, 2H, J=7.6 Hz), 2.63-2.58 (t, 2H, J=7.8 Hz), 0.24 (s, 9H); 13CNMR (CDCl3) δ 173.1, 141.1, 132.1, 128.2, 121.1, 105.0, 93.8, 51.6, 35.6, 30.8, 0.0.

Workup

  1. filtrationAfter filtration through Celite
  2. customthe product was obtained as a brown oil
  3. customused without purification in the next step

Sources & evidence

ORD record
ord-cdc67499f23645ba9f0e9082bedde206
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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