(E)-1-iodooct-1-en-3-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treatment of 63 g. (0.25 mole) of 1-iodo-trans-1-octen-3-one (Example 19) with sodium borohydride in the manner described in Example 21 gave 58 g. of yellow oil. The oil is purified by adsorption chromatography on a magnesia silica gel column using benzene as eluent to give a light yellow oil. gave 58 g The oil is purified by adsorption chromatography on a magnesia silica gel column to give a light yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treatment of 63 g. (0.25 mole) of 1-iodo-trans-1-octen-3-one (Example 19) with sodium borohydride in the manner described in Example 21 gave 58 g. of yellow oil. The oil is purified by adsorption chromatography on a magnesia silica gel column using benzene as eluent to give a light yellow oil. gave 58 g The oil is purified by adsorption chromatography on a magnesia silica gel column to give a light yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 54.5 g (0.364 mole) of sodium iodide and 40 g. (0.249 mole) of 1-chloro-trans-1-octen 3-one (Example 18) in 360 ml. of acetone is stirred and refluxed for 24 hours. The reaction mixture is cooled, filtered and concentrated. The residue is partitioned between water and ether. The organic phase is washed with dilute sodium bicarbonate solution, brine, dried (MgSO4) and evaporated to an oil. This material is used directly without purification. refluxed for 24 hours The reaction mixture is cooled filtered concentrated The residue is partitioned between water and ether The organic phase is washed with dilute sodium bicarbonate solution, brine dried (MgSO4) evaporated to an oil This material is used directly without purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 54.5 g (0.364 mole) of sodium iodide and 40 g. (0.249 mole) of 1-chloro-trans-1-octen 3-one (Example 18) in 360 ml. of acetone is stirred and refluxed for 24 hours. The reaction mixture is cooled, filtered and concentrated. The residue is partitioned between water and ether. The organic phase is washed with dilute sodium bicarbonate solution, brine, dried (MgSO4) and evaporated to an oil. This material is used directly without purification. refluxed for 24 hours The reaction mixture is cooled filtered concentrated The residue is partitioned between water and ether The organic phase is washed with dilute sodium bicarbonate solution, brine dried (MgSO4) evaporated to an oil This material is used directly without purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 78.2 g. (0.310 moles) of 1-iodo-trans-1-octen-3-one (Example 724) in 150 ml. of absolute ethanol is added dropwise over 2 hours to a slurry of 6.49 g. (0.172 moles) of sodium borohydride in 50 ml. of absolute ethanol cooled in an ice bath. After the addition is complete, the mixture is stirred for 2 hours with ice cooling and is then poured into 1 l. of water. The mixture is extracted into benzene and the organic phase is washed with saturated brine, dried (Na2SO4) and evaporated. The resulting oil is dissolved into 400 ml. of absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours to remove residual ketone. The mixture is cooled and evaporated and the residue is dissolved into 400 ml. of ether and is filtered. The filtrate is washed with dilute sodium bicarbonate solution and saturated brine, dried (Na2SO4), and evaporated to an oil. This oil is chromatographyed upon 2 Kg. of Florisil packed in hexane and the product is obtained upon elution with benzene Distillation of the product yields a colorless oil, b.p. 74°-76° C. (0.005 tor.). After the addition is then poured into 1 l The mixture is extracted into benzene the organic phase is washed with saturated brine dried (Na2SO4) evaporated The resulting oil is dissolved into 400 ml of absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours to remove residual ketone The mixture is cooled evaporated the residue is dissolved into 400 ml of ether and is filtered The filtrate is washed with dilute sodium bicarbonate solution and saturated brine dried (Na2SO4) evaporated to an oil the product is obtained upon elution with benzene Distillation of the product yields a colorless oil, b.p. 74°-76° C. (0.005 tor.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 78.2 g. (0.310 moles) of 1-iodo-trans-1-octen-3-one (Example 724) in 150 ml. of absolute ethanol is added dropwise over 2 hours to a slurry of 6.49 g. (0.172 moles) of sodium borohydride in 50 ml. of absolute ethanol cooled in an ice bath. After the addition is complete, the mixture is stirred for 2 hours with ice cooling and is then poured into 1 l. of water. The mixture is extracted into benzene and the organic phase is washed with saturated brine, dried (Na2SO4) and evaporated. The resulting oil is dissolved into 400 ml. of absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours to remove residual ketone. The mixture is cooled and evaporated and the residue is dissolved into 400 ml. of ether and is filtered. The filtrate is washed with dilute sodium bicarbonate solution and saturated brine, dried (Na2SO4), and evaporated to an oil. This oil is chromatographyed upon 2 Kg. of Florisil packed in hexane and the product is obtained upon elution with benzene Distillation of the product yields a colorless oil, b.p. 74°-76° C. (0.005 tor.). After the addition is then poured into 1 l The mixture is extracted into benzene the organic phase is washed with saturated brine dried (Na2SO4) evaporated The resulting oil is dissolved into 400 ml of absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours to remove residual ketone The mixture is cooled evaporated the residue is dissolved into 400 ml of ether and is filtered The filtrate is washed with dilute sodium bicarbonate solution and saturated brine dried (Na2SO4) evaporated to an oil the product is obtained upon elution with benzene Distillation of the product yields a colorless oil, b.p. 74°-76° C. (0.005 tor.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treatment of 63 g. (0.25 mole) of 1-iodo-trans-1-octen-3-one (Example 724) with sodium borohydride in the manner described in Example 726 gave 58 g. of yellow oil. The oil is purified by adsorption chromatography on a magnesia silica gel column using benzene as eluent to give a light yellow oil. gave 58 g The oil is purified by adsorption chromatography on a magnesia silica gel column to give a light yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treatment of 63 g. (0.25 mole) of 1-iodo-trans-1-octen-3-one (Example 724) with sodium borohydride in the manner described in Example 726 gave 58 g. of yellow oil. The oil is purified by adsorption chromatography on a magnesia silica gel column using benzene as eluent to give a light yellow oil. gave 58 g The oil is purified by adsorption chromatography on a magnesia silica gel column to give a light yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 54.5 g. (0.364 mole) of sodium iodide and 40 g. (0.249 mole) of 1-chloro-trans-1-octen 3-one (Example 723) in 360 ml. of acetone is stirred and refluxed for 24 hours. The reaction mixture is cooled, filtered and concentrated. The residue is partitioned between water and ether. The organic phase is washed with dilute sodium bicarbonate solution, brine, dried (MgSO4) and evaporated to an oil. This material is used directly without purification. A mixture of 54.5 g refluxed for 24 hours The reaction mixture is cooled filtered concentrated The residue is partitioned between water and ether The organic phase is washed with dilute sodium bicarbonate solution, brine dried (MgSO4) evaporated to an oil This material is used directly without purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 54.5 g. (0.364 mole) of sodium iodide and 40 g. (0.249 mole) of 1-chloro-trans-1-octen-3-one (Example 222) in 360 ml. of acetone is stirred and refluxed for 24 hours. The reaction mixture is cooled, filtered and concentrated. The residue is partitioned between water and ether. The organic phase is washed with dilute sodium bicarbonate solution, brine, dried (MgSO4) and evaporated to an oil. This material is used directly without purification. A mixture of 54.5 g refluxed for 24 hours The reaction mixture is cooled filtered concentrated The residue is partitioned between water and ether The organic phase is washed with dilute sodium bicarbonate solution, brine dried (MgSO4) evaporated to an oil This material is used directly without purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 78.2 g. (0.310 moles) of 1-iodo-trans-1-octen-3-one (Example 724) in 150 ml. of absolute ethanol is added dropwise over 2 hours to a slurry of 6.49 g. (0.172 moles) of sodium borohydride in 50 ml. of absolute ethanol cooled in an ice bath. After the addition is complete, the mixture is stirred for 2 hours with ice cooling and is then poured into 1 l. of water. The mixture is extracted into benzene and the organic phase is washed with saturated brine, dried (Na2SO4) and evaporated. The resulting oil is dissolved into 400 ml. of absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours to remove residual ketone. The mixture is cooled and evaporated and the residue is dissolved into 400 ml. of ether and is filtered. The filtrate is washed with dilute sodium bicarbonate solution and saturated brine, dried (Na2SO4), and evaporated to an oil. This oil is chromatographyed upon 2 Kg. of Florisil® packed in hexane and the product is obtained upon elution with benzene Distillation of the product yields a colorless oil, b.p. 74°-76° C. (0.005 tor.). After the addition is then poured into 1 l The mixture is extracted into benzene the organic phase is washed with saturated brine dried (Na2SO4) evaporated The resulting oil is dissolved into 400 ml of absolute ethanol and treated with 5 mole percent of p-carboxyphenylhydrazine at 70° C. for 1.5 hours to remove residual ketone The mixture is cooled evaporated the residue is dissolved into 400 ml of ether and is filtered The filtrate is washed with dilute sodium bicarbonate solution and saturated brine dried (Na2SO4) evaporated to an oil the product is obtained upon elution with benzene Distillation of the product yields a colorless oil, b.p. 74°-76° C. (0.005 tor.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Treatment of 63 g. (0.25 mole) of 1-iodo-trans-1-octen-3-one (Example 724) with sodium borohydride in the manner described in Example 726 gave 58 g. of yellow oil. The oil is purified by adsorption chromatography on a magnesia silica gel column using benzene as eluent to give a light yellow oil. gave 58 g The oil is purified by adsorption chromatography on a magnesia silica gel column to give a light yellow oil