Reaktion #2035328

Reaktionsgleichung

8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile

1,4-dioxa-spiro[4.5]decane-8-carbonitrile

cyclopropylmethyl bromide

citric acid

diisobutylaluminium hydride

toluene

→

8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas recooled to −78° C.
2. 2
   Temperaturwarmed to room temperature
3. 3
   SonstigeThe mixture was partitioned between methyl-tert.butyl ether and water
4. 4
   Extraktionthe aqueous phase extracted twice with methyl-tert.butyl ether
5. 5
   Trocknenthe combined organics were dried over magnesium sulphate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated

Vorschrift

To a solution of 8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile, prepared from 1,4-dioxa-spiro[4.5]decane-8-carbonitrile and cyclopropylmethyl bromide in a similar fashion as described for 5, (3.00 g, 13.6 mmol) in tetrahydrofuran (40 mL) at −78° C. was added a 1M solution of diisobutylaluminium hydride in toluene (20.3 mL, 20.3 mmol, 1.5 eq.) and the reaction was allowed to warmed to 0° C. over a period of 3 h. The mixture was recooled to −78° C., neutralized by dropwise addition of a 10% aqueous citric acid solution and warmed to room temperature. The mixture was partitioned between methyl-tert.butyl ether and water, the aqueous phase extracted twice with methyl-tert.butyl ether and the combined organics were dried over magnesium sulphate, filtered and evaporated to give 8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde.

Quelle