benzyl but-3-enoate

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

Procedure: Using a procedure analogous to that used to prepare 8A, benzyl but-3-enoate (3.63 g, 0.020 mmol, reference for preparation: Cardillo, G.; De Simone, A.; Mingardi, A.; Tomasini, C. Synlett 1995, 11, 1131-2) was reacted with 4-bromo-2-ethyl-iodobenzene (6.23 g, 0.020 mmol) to give 21A (1.5 g, 21%). 1H NMR (400 MHz, CDCl3) δ ppm 1.18 (t, J=7.69 Hz, 3 H) 1.84-1.94 (m, 2 H) 2.41 (t, J=7.25 Hz, 2 H) 2.55-2.62 (m, 4 H) 5.12 (s, 1 H) 6.96 (d, J=7.91 Hz, 1 H) 7.22 (dd, J=7.91, 2.20 Hz, 1 H) 7.29 (d, J=2.20 Hz, 1 H) 7.30-7.40 (m, 5 H). for preparation

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

Procedure: 138 g (535 mmol) Triphenylphosphine and 84 ml (812 mmol) benzyl alcohol were added dropwise to 46 g (535 mmol) 3-butenoic acid dissolved in 500 ml ether and 87 ml (535 mmol) ethyl azodicarboxylate and the mixture stirred for 7 hours and allowed to stand overnight. After evaporation of the solvent, the residue was purified by column chromotography (silica gel, hexane/ethyl acetate=95:5) and a sample analysed by thin layer chromatography (hexane:ethyl acetate=1:1) (Rf=0.61). After evaporation of the solvent the residue was purified by column chromotography (silica gel, hexane/ethyl acetate=95:5)

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

Procedure: 138 g (535 mmol) Triphenylphosphine and 84 ml (812 mmol) benzyl alcohol were added dropwise to 46 g (535 mmol) 3-butenoic acid dissolved in 500 ml ether and 87 ml (535 mmol) ethyl azodicarboxylate and the mixture stirred for 7 hours and allowed to stand overnight. After evaporation of the solvent, the residue was purified by column chromotography (silica gel, hexane/ethyl acetate=95:5) and a sample analysed by thin layer chromatography (hexane:ethyl acetate=1:1) (Rf=0.61). After evaporation of the solvent the residue was purified by column chromotography (silica gel, hexane/ethyl acetate=95:5)

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

Procedure: Using a procedure analogous to that used to prepare 8A, benzyl but-3-enoate (3.63 g, 0.020 mmol, reference for preparation: Cardillo, G.; De Simone, A.; Mingardi, A.; Tomasini, C. Synlett 1995, 11, 1131-2) was reacted with 4-bromo-2-ethyl-iodobenzene (6.23 g, 0.020 mmol) to give 21A (1.5 g, 21%). 1H NMR (400 MHz, CDCl3) δ ppm 1.18 (t, J=7.69 Hz, 3 H) 1.84-1.94 (m, 2 H) 2.41 (t, J=7.25 Hz, 2 H) 2.55-2.62 (m, 4 H) 5.12 (s, 1 H) 6.96 (d, J=7.91 Hz, 1 H) 7.22 (dd, J=7.91, 2.20 Hz, 1 H) 7.29 (d, J=2.20 Hz, 1 H) 7.30-7.40 (m, 5 H). for preparation

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

Procedure: 138 g (535 mmol) Triphenylphosphine and 84 ml (812 mmol) benzyl alcohol were added dropwise to 46 g (535 mmol) 3-butenoic acid dissolved in 500 ml ether and 87 ml (535 mmol) ethyl azodicarboxylate and the mixture stirred for 7 hours and allowed to stand overnight. After evaporation of the solvent, the residue was purified by column chromotography (silica gel, hexane/ethyl acetate=95:5) and a sample analysed by thin layer chromatography (hexane:ethyl acetate=1:1) (Rf=0.61). After evaporation of the solvent the residue was purified by column chromotography (silica gel, hexane/ethyl acetate=95:5)