Reacción #1824330

Ecuación de reacción

ethyl cyclohexylideneacetate

lithium aluminium hydride

→

2-cyclohexylidene ethanol

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrobefore quenching with dilute hydrochloric acid (2M; 20 ml)
2. 2
   FiltraciónThe mixture was filtered
3. 3
   Otrothe aqueous layer was separated
4. 4
   Extracciónextracted further with ether (2×25 ml)
5. 5
   Lavadothe combined ether layers washed with water (2×25 ml) and saturated sodium chloride solution (25 ml)
6. 6
   Secadodried over MgSO4
7. 7
   FiltraciónFiltration and evaporation of the solvent and distillation of the residue

Procedimiento

To a stirred solution of ethyl cyclohexylideneacetate (see route to this by Wadsworth and Emmons in Org. Synth. Coll. Vol 5 547) (3.00 g, 17.8 mmol) in dry ether (50 ml) under an atmosphere of nitrogen at 0° C. was added lithium aluminium hydride (407 mg, 10.7 mol) portionwise and the mixture stirred for 2 hours before quenching with dilute hydrochloric acid (2M; 20 ml). The mixture was filtered and the aqueous layer was separated and extracted further with ether (2×25 ml) and the combined ether layers washed with water (2×25 ml) and saturated sodium chloride solution (25 ml) and then dried over MgSO4. Filtration and evaporation of the solvent and distillation of the residue gave 2-cyclohexylidene ethanol (2.16 g, bp. 112° C. at 10 mmHg [Kugelrohr]).

Fuente