(E)-dec-5-en-1-ol

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

Procedure: DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 266 mg (72%) of colorless liquid. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc) Evaporation of the solvent

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

Procedure: DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 266 mg (72%) of colorless liquid. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc) Evaporation of the solvent

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

Procedure: DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 266 mg (72%) of colorless liquid. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc) Evaporation of the solvent

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

Procedure: DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 266 mg (72%) of colorless liquid. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc) Evaporation of the solvent

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

Procedure: DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 266 mg (72%) of colorless liquid. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc) Evaporation of the solvent

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

Procedure: FIG. 16 shows a synthesis of 5-decenyl acetate which involves the cross-metathesis of vinyl borate pinacol ester (Matheson, D. S J Am Chem Soc (1960) 82, 4228-4233) with 5-hexenol THP ether (or 1,10-diTHP ether of 5-decene) with Catalyst 823 to yield a pinacol ester of 1-borohexen-6-ol THP ether. This product was coupled with butyl lithium and zinc chloride under Suzuki conditions as described by Miycuira (Org Syn VIII p 532) to yield E-5-decenol THP ether in a 91:9 E:Z isomeric ratio. This material was purified by column chromatography and then acetated to yield 5-decenyl acetate in 91:9 E:Z isomeric ratio.

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

Procedure: A solution of DEAD (0.261 g, 1.50 mmol) in THF (20) was added dropwise to a stirred solution of 4-[5-(5,5,6,6,7,7,8,8,8-nonafluorooctyloxy)-pyrimidin-2-yl]-phenol (0.693 g, 1.50 mmol), trans-5-decen-1-ol (0.234 g, 1.50 mmol) and triphenylphosphine (0.399 g, 1.50 mmol) in THF (30) and the reaction mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and the residues purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1)] to yield a colorless solid, which was recrystallized from ethanol. The solvent was removed in vacuo the residues purified by column chromatography [silica gel, eluted with hexane/ethyl acetate (4:1)] to yield a colorless solid, which was recrystallized from ethanol

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

Procedure: DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 266 mg (72%) of colorless liquid. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc) Evaporation of the solvent

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

Procedure: DEAD (256 mg, 1.47 mmol), phenol 34 (194 mg, 1.28 mmol), alcohol 26j (200 mg, 1.28 mmol), and TPP (386 mg, 1.47 mmol) in 13 ml anhydrous ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc). Evaporation of the solvent yielded 266 mg (72%) of colorless liquid. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5 to 90/10 (v/v, Hex/EtOAc) Evaporation of the solvent