Benzyl Bromide → ((Pent-4-yn-1-yloxy)methyl)benzene

HRID 1522999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522999
[H-].[Na+].[C:3]([OH:8])#[C:4][CH2:5][CH2:6][CH3:7].[CH:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[CH:11][CH:10]=1>C1COCC1>[CH2:3]([O:8][CH2:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)[CH2:4][CH2:5][C:6]#[CH:7]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10866258Pentynol

Produkt 1

HCID 563055((Pent-4-yn-1-yloxy)methyl)benzeneAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a flame-dried round-bottomed flask was added NaH (2 equiv., 47.6 mmol, 1.9 g of a 60% dispersion in mineral oil). The solid was washed with hexanes (15 mL), THF (95 mL) was added and the suspension was cooled to 0° C. Pentynol (1 equiv., 23.8 mmol, 2.0 g) was added drop wise in THF (5 mL), followed by drop wise addition of BnBr (0.92 equiv., 21.9 mmol, 2.60 mL). The reaction was warmed to ambient temperature over 16 h, quenched with saturated aqueous NH4Cl (25 mL), and diluted with water (20 mL). The organic layer was extracted with EtOAc (2×40 mL), washed with brine (40 mL) and dried with Na2SO4. Product isolation was achieved by concentration in vacuo and purification by flash column chromatography to afford ((pent-4-yn-1-yloxy)methyl)benzene (3.60 g, 20.7 mmol, 94%). TLC Rf=0.41 (5% EtOAc/Hex); 1HNMR (300 MHz): δ 7.29-7.44 (5H), 4.55 (s, 2H), 3.61 (t, 2H, J=6.2 Hz), 2.36 (td, 2H, J=7.1, 2.6 Hz), 1.97 (t, 1H, J=2.6 Hz), 1.81-1.93 (m, 2H). 13CNMR (75 MHz): δ 138.5, 128.4, 127.63, 127.58, 84.0, 73.0, 68.7, 68.5, 28.7, 15.3.

Aufarbeitung

  1. washThe solid was washed with hexanes (15 mL), THF (95 mL)
  2. additionwas added
  3. temperatureThe reaction was warmed to ambient temperature over 16 h
  4. customquenched with saturated aqueous NH4Cl (25 mL)
  5. additiondiluted with water (20 mL)
  6. extractionThe organic layer was extracted with EtOAc (2×40 mL)
  7. washwashed with brine (40 mL)
  8. dry with materialdried with Na2SO4
  9. concentrationProduct isolation was achieved by concentration in vacuo and purification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1c270ea69f4a471898ae4bfccba67568
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079835B2

Notizen zur Reaktion

Wird geladen…