Reaktion #9405

Reaktionsgleichung

22

2,3-diisopropoxy-4-methoxybenzaldehyde

methyllithium

→

alcohol

Ausbeute 84.0%

2,3-diisopropoxy-1-(1-hydroxyethyl)-4-methoxybenzene

Ausbeute 84.0%

Lösungsmittel

ethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeallowing too reach room temperature
2. 2
   SonstigeThe reaction was slowly quenched with water
3. 3
   Sonstigethe phases were separated
4. 4
   Extraktionthe aqueous phase was extracted with ethyl ether (3×150 mL)
5. 5
   TrocknenThe combined organic solutions were dried over MgSO4
6. 6
   Einengenconcentrated over reduced pressure
7. 7
   SonstigePurification
8. 8
   Waschenby flash column chromatography (silica gel, elution with hexanes/EtOAc: 80/20)

Vorschrift

To a solution of 22 (23.10 g, 91.56 mmol) in dry ethyl ether (150 mL) was added dropwise methyllithium (98.10 mL, 1.4 M in EtO2, 1.37.3 mmol) at 0° C. under nitrogen. The reaction mixture was stirred for 2 h allowing too reach room temperature. The reaction was slowly quenched with water, the phases were separated, and the aqueous phase was extracted with ethyl ether (3×150 mL). The combined organic solutions were dried over MgSO4 and concentrated over reduced pressure. Purification by flash column chromatography (silica gel, elution with hexanes/EtOAc: 80/20) provided the protected alcohol 20.62 g (76.77 mmol, 84%) as a pale yellow oil.

Quelle