Reaktion #95933

Reaktionsgleichung

methanol

7-bromoheptanoic acid t-butyl ester

hydride

water

→

title compound

Ausbeute 85.3%

7-bromoheptanaldehyde

Ausbeute 85.3%

Lösungsmittel

methylene chloride

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 30° C. to 40° C. for 1 hour
2. 2
   FiltrationThe deposited crystals were filtered out
3. 3
   Einengenthe filtrate was concentrated under reduced pressure
4. 4
   SonstigeThe residue was purified by column chromatography on silica gel using
5. 5
   workup.ADDITIONa mixture of methylene and chloride and cyclohexane (1:1) as an eluent

Vorschrift

To 8.5 g of 7-bromoheptanoic acid t-butyl ester (prepared as described in Reference Example 1) in 80 ml of methylene chloride was added dropwise 18.2 ml of a 25% solution of diisobutyl alminium hydride in toluene at -78° C. over a period of 1 hours. The solution was stirred at the same temperature, to which was added 5 ml of methanol at from 0° C. to 10° C. and then added 10 ml of water, and the mixture was stirred at 30° C. to 40° C. for 1 hour. The deposited crystals were filtered out, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of methylene and chloride and cyclohexane (1:1) as an eluent to give 5.28 g of the title compound having the following physical characteristic:

Quelle