Sodium hydride → HCID 59557729, Verbindung

HRID 1175323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175323
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][OH:22].[H-].[Na+].Br[CH2:26][C:27]#[C:28][CH3:29]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][O:22][CH2:26][C:27]#[C:28][CH3:29]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 595577063-(2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol

Produkt 1

HCID 59557729HCID 59557729, VerbindungAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-(2-bromo-5-chloro-4-(4-ethoxybenzyl)phenyl)propan-1-ol (BL) (0.268 g, 0.70 mmol) in 5 mL of THF was added NaH (0.034 g, 0.84 mmol, 60%) and stirred for 40 min. 1-bromo-2-butyne (0.094 mL, 1.05 mmol) was added and the mixture was stirred overnight at room temperature. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, concentrated and purified by preparative TLC (eluting with EtOAc:PE=1:10) to obtain 0.2 g of intermediate BM.

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by preparative TLC (eluting with EtOAc:PE=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-754414dff5ca4009b086c461394b7518
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838498B2

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