5-pentan-3-ylidenecyclopenta-1,3-diene

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

Procedure: To a solution of 8.00 g (59.6 mol) of 6,6-diethylfulvene in 35 ml of ether, 60.0 ml (68.4 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (92° C./40 mmHg) to obtain 5.50 g (36.6 mmol) of a light yellow liquid (yield: 61%). The analyzed values are given below. The separated organic phase was washed with water a saturated saline solution, then dried over magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (92° C./40 mmHg)

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

Procedure: To a solution of 8.00 g (59.6 mol) of 6,6-diethylfulvene in 35 ml of ether, 60.0 ml (68.4 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (92° C./40 mmHg) to obtain 5.50 g (36.6 mmol) of a light yellow liquid (yield: 61%). The analyzed values are given below. The separated organic phase was washed with water a saturated saline solution, then dried over magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (92° C./40 mmHg)

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

Procedure: To a solution of 22.00 g (332.8 mmol) of cyclopentadiene in 35 ml of methanol, 36.0 ml (665.1 mmol) of diethyl ketone and 28.0 ml (335.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 200 ml of ether, 100 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (78-83° C./4 mmHg) to obtain 36.50 g (271.94 mmol) of a yellow liquid (yield: 82%). The analyzed values are given below. was added The organic phase was separated washed with water a saturated saline solution, then dried over anhydrous magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (78-83° C./4 mmHg)

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

Procedure: To a solution of 22.00 g (332.8 mmol) of cyclopentadiene in 35 ml of methanol, 36.0 ml (665.1 mmol) of diethyl ketone and 28.0 ml (335.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 200 ml of ether, 100 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (78-83° C./4 mmHg) to obtain 36.50 g (271.94 mmol) of a yellow liquid (yield: 82%). The analyzed values are given below. was added The organic phase was separated washed with water a saturated saline solution, then dried over anhydrous magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (78-83° C./4 mmHg)

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

Procedure: To a solution of 8.00 g (59.6 mmol) of 6,6-diethylfulvene in 35 ml of ether, 60.0 ml (68.4 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (92° C./40 mmHg) to obtain 5.50 g (36.6 mmol) of a light yellow liquid (yield: 61%). The analyzed values are given below. The separated organic phase was washed with water a saturated saline solution, then dried over magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (92° C./40 mmHg)

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

Procedure: To a solution of 22.00 g (332.8 mmol) of cyclopentadiene in 35 ml of methanol, 36.0 ml (665.1 mmol) of diethyl ketone and 28.0 ml (335.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 200 ml of ether, 100 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (78-83° C./4 mmHg) to obtain 36.50 g (271.94 mmol) of a yellow liquid (yield: 82%). The analyzed values are given below. was added The organic phase was separated washed with water a saturated saline solution, then dried over anhydrous magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (78-83° C./4 mmHg)

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

Procedure: To a solution of 22.00 g (332.8 mmol) of cyclopentadiene in 35 ml of methanol, 36.0 ml (665.1 mmol) of diethyl ketone and 28.0 ml (335.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 200 ml of ether, 100 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (78-83° C./4 mmHg) to obtain 36.50 g (271.94 mmol) of a yellow liquid (yield: 82%). The analyzed values are given below. was added The organic phase was separated washed with water a saturated saline solution, then dried over anhydrous magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (78-83° C./4 mmHg)

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

Procedure: To a solution of 8.00 g (59.6 mol) of 6,6-diethylfulvene in 35 ml of ether, 60.0 ml (68.4 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (92° C./40 mmHg) to obtain 5.50 g (36.6 mmol) of a light yellow liquid (yield: 61%). The analyzed values are given below. The separated organic phase was washed with water a saturated saline solution, then dried over magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (92° C./40 mmHg)

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

Procedure: To a solution of 22.00 g (332.8 mmol) of cyclopentadiene in 35 ml of methanol, 36.0 ml (665.1 mmol) of diethyl ketone and 28.0 ml (335.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 200 ml of ether, 100 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (78-83° C./4 mmHg) to obtain 36.50 g (271.94 mmol) of a yellow liquid (yield: 82%). The analyzed values are given below. was added The organic phase was separated washed with water a saturated saline solution, then dried over anhydrous magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (78-83° C./4 mmHg)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6,6-diethyl-fulvene (prepared as described in J. Org. Chem., 1990, 55, 3395; 86.0 g, 0.64 mol) and methyl-vinyl-ketone (44.9 g, 0.64 mol) was stirred for 5 h at 50° C. The mixture was cooled to room temperature and diluted with toluene/hexane (1/9, 600 ml). The solution was hydrogenated at normal pressure using palladium on charcoal (10%) as a catalyst. After 5 h the mixture was filtered, concentrated in vacuo and the residue was distilled (bp. 70° C./0.01 Torr) to yield the title compound (65.5 g, 50%) as a mixture of 2 isomers in a ratio of 3:1. Odor description: Woody, floral, Vertofix, Lilial, ambery. The mixture was cooled to room temperature After 5 h the mixture was filtered concentrated in vacuo the residue was distilled (bp. 70° C./0.01 Torr)

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

Procedure: To a solution of 8.00 g (59.6 mmol) of 6,6-diethylfulvene in 35 ml of ether, 60.0 ml (68.4 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for one night. Then, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (92° C./40 mmHg) to obtain 5.50 g (36.6 mmol) of a light yellow liquid (yield: 61%). The analyzed values are given below. The separated organic phase was washed with water a saturated saline solution, then dried over magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (92° C./40 mmHg)

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

Procedure: To a solution of 22.00 g (332.8 mmol) of cyclopentadiene in 35 ml of methanol, 36.0 ml (665.1 mmol) of diethyl ketone and 28.0 ml (335.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for one night. After the reaction solution was diluted with 200 ml of ether, 100 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (78-83° C./4 mmHg) to obtain 36.50 g (271.94 mmol) of a yellow liquid (yield: 82%). The analyzed values are given below. was added The organic phase was separated washed with water a saturated saline solution, then dried over anhydrous magnesium sulfate filtered From the filtrate, the solvent was removed under reduced pressure to obtain a liquid The liquid was subjected to vacuum distillation (78-83° C./4 mmHg)