Methyl iodide → Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)propanoate

HRID 1473065

Reaktionsgleichung

Reaktionsgleichung von HRID 1473065
[Li+].[CH3:2]C([N-]C(C)C)C.[CH3:9][Si:10]([C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][C:22]([O:24][CH3:25])=[O:23])([CH3:12])[CH3:11].CI>C1COCC1>[CH3:11][Si:10]([C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]([CH3:2])[C:22]([O:24][CH3:25])=[O:23])([CH3:12])[CH3:9]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 59457733Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

Produkt 1

HCID 71209064Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2 M LDA solution (1.24 mL, 2.48 mmol) was added to solution of methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate (I10) (0.306 g, 1.24 mmol) in THF (10 mL) at −78° C. and the mixture stirred for 30 minutes. Methyl iodide was then added (0.155 mL, 2.48 mmol) and the reaction mixture slowly warmed to room temperature over 1.5 hours. The reaction mixture was then left to stir at room temperature for 18 hours before quenching with a saturated solution of NH4Cl (20 mL). EtOAc (20 mL) was then added and the layers separated. The aqueous layer was further extracted with EtOAc (2×20 mL). The solvent was removed in vacuo to give a brown oil which was purified by column chromatography on silica gel (0-5% EtOAc in petroleum benzine 40-60° C.) to afford the title compound (I50) (0.297 g, 92%) as a yellow oil; 1H NMR (400 MHz, CDCl3) δ7.49-7.44 (m, 1H), 7.33-7.24 (m, peaks obscured by CDCl3), 7.21-7.17 (m, 1H), 4.25 (q, J=7.2 Hz, 1H), 3.67 (s, 3H), 1.51 (d, J=7.2 Hz, 3H), 0.26 (s, 9H).

Aufarbeitung

  1. waitThe reaction mixture was then left
  2. stirringto stir at room temperature for 18 hours
  3. custombefore quenching with a saturated solution of NH4Cl (20 mL)
  4. additionEtOAc (20 mL) was then added
  5. customthe layers separated
  6. extractionThe aqueous layer was further extracted with EtOAc (2×20 mL)
  7. customThe solvent was removed in vacuo
  8. customto give a brown oil which
  9. customwas purified by column chromatography on silica gel (0-5% EtOAc in petroleum benzine 40-60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-49668fb07fe84c84b9a9b37cd832ac45
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012461B2

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