(Z)-dec-5-ene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: In contrast to the “classical” ruthenium metathesis catalysts mentioned above, which react only with highly-strained olefins, alkylidenes 6 and 7 of Example 6 also promote the ROMP of less-strained monomers such as 1,5-cyclooctadiene, and are active in the metathesis of acyclic olefins in protic solvents. For example, 6 will dimerize 1-hexene in methanol to give 5-decene in 20% yield (Equation 3). In these systems, separation of catalyst from product is facilitated through addition of water to the reaction mixture. Olefins collected from the resulting two-phase system contain very low levels of detectable ruthenium.

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

Procedure: A process for preparing 9-tetradecenyl alcohol by reacting 1-hexene or 5-decene with 9-decenyl acetate in accordance with the method of claim 7 to obtain tetradecenyl acetate and then reacting the acetate with water to obtain said alcohol.

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

Procedure: A process for preparing 9-tetradecenyl formate by reacting 1-hexene or 5-decene with 9-decenyl acetate in accordance with the method of claim 7 to obtain 9-tetradecenyl acetate, then reacting the acetate with water to obtain the corresponding alcohol and then reacting the alcohol with formic acid to obtain the formate.

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: Following the procedure outlined for the preparation of Example 1, N-[4-(5-hydroxy-pyridin-2-yloxy)-benzyl]-acetamide (0.25 g, 0.97 mmol) when treated with 5-bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione (0.20 g, 0.80 mmol), 1,5,7-trazabicyclo[4.4.0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (PTBD, Fluka, 0.77 g) and 4 mL of acetonitrile, will afford N-(4-{5-[5-(2-Ethoxy-ethyl)-2,4,6-trioxo-hexahydro-pyrimidin-5-yloxy]-pyridin-2-yloxy}-benzyl)-acetamide. Expected MS (m/z, APCI): 455 [M−H]−.

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

Procedure: Following the procedure outlined for the preparation of Example 1, 4-(4-aminomethyl-phenoxy)-phenol (0.70 g, 3.32 mmol) was reacted with 5-bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione (0.95 g, 2.4 mmol), 1,5,7-trazabicyclo[4.4.0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (PTBD, Fluka, 2.22 9) and 11 mL of acetonitrile, affording 5-[4-(4-aminomethyl-phenoxy)-phenoxy]-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione (0.180 g) as a colorless solid after purification by reverse phase HPLC.

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

Procedure: Following the procedure outlined for the preparation of Example 1 4-(4-hydroxy-phenoxy)-N-methyl-benzamide (0.14 g, 0.58 mmol) was reacted with 5-bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione (0.16 g, 0.58 mmol), 1,5,7-trazabicyclo[4.4.0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (PTBD, Fluka, 0.40 g) and 2.0 mL of acetonitrile, affording 4-{4-[5-(2-ethoxy-ethyl)-2,4,6-trioxo-hexahydro-pyrimidin-5-yloxy]-phenoxy}-N-methyl-benzamide (0.040 g) as a colorless solid.

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

Procedure: Following the procedure outlined for the preparation of Example 1, N-[4-(4-hydroxy-phenoxy)-benzyl]-propionamide (0.13 g, 0.47 mmol) was reacted with 5-bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione (0.13 g, 0.48 mmol), 1,5,7-trazabicyclo[4.4.0]dec-5-ene bound to polystyrene crosslinked with 2% DVB (PTBD, Fluka, 0.31 g) and 1.55 mL of acetonitrile, benzyl)-propionamide (0.060 g) as a colorless solid.