(E)-3-(3-bromophenyl)prop-2-en-1-ol

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

Procedure: A magnetically stirred solution of m-chloroperbenzoic acid (3.57 g, 10.33 mmol) in dichloromethane (60.0 ml) at 25° C. was treated dropwise with a solution of trans-3-(3-bromophenyl)-2-propenol (2.0 g, 9.39 mmol) in dichloromethane (20.0 ml). After stirring for 16 h the mixture was diluted with dichloromethane (200 ml), washed with aqueous 1M NaOH (2×200 ml), brine (2×200 ml) and dried (Na2SO4). Evaporation of the solvent in vacuo returned the crude epoxide as a pale yellow oil (2.06 g). Column chromatography (ethyl acetate--light petroleum (b.p. 40°-60° C.), 3:7) provided the title compound (1.53 g, 71%) as a pale yellow oil. washed with aqueous 1M NaOH (2×200 ml), brine (2×200 ml) dried (Na2SO4) Evaporation of the solvent in vacuo

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

Procedure: The title compound was prepared from trans-3-(3-bromophenyl)-2-propenol by a sequence analogous to that described above for compound (9a) but using D-(-)-diethyl tartrate. Column chromatography (ethyl acetate--light petroleum (b.p. 40°-60° C.), 3:7) provided the title compound (73%) as a pale yellow oil. Distilled at 160°-185° C. at 0.1 mmHg. using a Kugelrohr short path distillation apparatus as a colourless oil; [α]D25 +37.6 (c=0.020 gml-1, CHCl3).

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vigorously stirred solution of ethyl trans-3-(3-bromophenyl)-2-propenoate (26.71 g, 0.105 mol) in dry toluene (150 ml) at -5° C. (ice-EtOH) under nitrogen was treated with lithium aluminium hydride (3.98 g, 0.105 mol) in one portion. The reaction temperature was allowed to gradually warm to room temperature over 30 min., at 25° C. the reaction became quite exothermic (25°-40° C.) with the formation of a grey gelatinous precipitate. Stirring was continued for 1 h, after which the reaction was carefully quenched with water (300 ml) and ice (200 g) then allowed to stand at 25° C. for 30 min. The mixture was filtered through Celite (Registered Trade Mark) and the residue was washed with ethyl acetate (2×200 ml). The filtrate was extracted with the organic washings, the combined organic phases were washed with brine (3×300 ml), water (300 ml), dried (Na2SO4) and evaporated to give the title compound as a pale yellow oil (21.42 g, 96%). Distillation at 120° C. at 0.05 mmHg. gave a colourless oil. (Found C, 50.73; H, 4.12; Br, 37.53. C9H9BrO requires C, 50.73; H, 4.26; Br, 37.50%); νmax (thin film)/cm-1 3325.5 (br. OH), 2862.0, 1653.0, 1591.0, 1562.5; δH (270 MHz) 2.15 (1H, bs, 1-OH), 4.30 (2H, dd, 2×1-H, 3J1,2 =5.5, 4J1,3 1.5 Hz), 6.33 (1H, dt, 2-H, 3J2,3 =15.8, 3J2,1 =5.3 Hz), 6.53 (1H, dt, 3-H, 3J3,2 =16.2, 4J3,1 =1.3 Hz), 7.15 (1H, t, 5'-H, Jo =7.8 Hz), 7.26 (1H, dt, 6'-H, Jo =7.6, Jm =1.3 Hz), 7.35 (1H, dt, 4'-H, Jo =7.9, Jm =1.6 Hz), 7.50 (1H, t, 2'-H, Jm =1.6 Hz). δC (67.8 MHz) 63.2 (1-C), 122.7 (3'-C), 125.0 (2-C), 129.2 (5'-H), 138.8 (1'-C). The remaining signals fall in the narrow range 130.0 to 130.4 ppm; m/z 214.1, 212.1 (44.86,49.78, M+), 196.0, 194.0 (1.47, 1.03), 185.0, 183.0 (10.81, 12.19), 172.0, 170.0 (46.47, 49.07), 158.0, 156.0 (15.47, 15.80), 133.1, 131.1 (36.29, 25.66), 104.1 (100). (25°-40° C.) after which the reaction was carefully quenched with water (300 ml) and ice (200 g) to stand at 25° C. for 30 min The mixture was filtered through Celite (Registered Trade Mark) the residue was washed with ethyl acetate (2×200 ml) The filtrate was extracted with the organic washings the combined organic phases were washed with brine (3×300 ml), water (300 ml) dried (Na2SO4) evaporated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vigorously stirred solution of ethyl trans-3-(3-bromophenyl)-2-propenoate (26.71 g, 0.105 mol) in dry toluene (150 ml) at -5° C. (ice-EtOH) under nitrogen was treated with lithium aluminium hydride (3.98 g, 0.105 mol) in one portion. The reaction temperature was allowed to gradually warm to room temperature over 30 min., at 25° C. the reaction became quite exothermic (25°-40° C.) with the formation of a grey gelatinous precipitate. Stirring was continued for 1 h, after which the reaction was carefully quenched with water (300 ml) and ice (200 g) then allowed to stand at 25° C. for 30 min. The mixture was filtered through Celite (Registered Trade Mark) and the residue was washed with ethyl acetate (2×200 ml). The filtrate was extracted with the organic washings, the combined organic phases were washed with brine (3×300 ml), water (300 ml), dried (Na2SO4) and evaporated to give the title compound as a pale yellow oil (21.42 g, 96%). Distillation at 120° C. at 0.05 mmHg. gave a colourless oil. (Found C, 50.73; H, 4.12; Br, 37.53. C9H9BrO requires C, 50.73; H, 4.26; Br, 37.50%); νmax (thin film)/cm-1 3325.5 (br. OH), 2862.0, 1653.0, 1591.0, 1562.5; δH (270 MHz) 2.15 (1H, bs, 1-OH), 4.30 (2H, dd, 2×1-H, 3J1,2 =5.5, 4J1,3 1.5 Hz), 6.33 (1H, dt, 2-H, 3J2,3 =15.8, 3J2,1 =5.3 Hz), 6.53 (1H, dt, 3-H, 3J3,2 =16.2, 4J3,1 =1.3 Hz), 7.15 (1H, t, 5'-H, Jo =7.8 Hz), 7.26 (1H, dt, 6'-H, Jo =7.6, Jm =1.3 Hz), 7.35 (1H, dt, 4'-H, Jo =7.9, Jm =1.6 Hz), 7.50 (1H, t, 2'-H, Jm =1.6 Hz). δC (67.8 MHz) 63.2 (1-C), 122.7 (3'-C), 125.0 (2-C), 129.2 (5'-H), 138.8 (1'-C). The remaining signals fall in the narrow range 130.0 to 130.4 ppm; m/z 214.1, 212.1 (44.86,49.78, M+), 196.0, 194.0 (1.47, 1.03), 185.0, 183.0 (10.81, 12.19), 172.0, 170.0 (46.47, 49.07), 158.0, 156.0 (15.47, 15.80), 133.1, 131.1 (36.29, 25.66), 104.1 (100). (25°-40° C.) after which the reaction was carefully quenched with water (300 ml) and ice (200 g) to stand at 25° C. for 30 min The mixture was filtered through Celite (Registered Trade Mark) the residue was washed with ethyl acetate (2×200 ml) The filtrate was extracted with the organic washings the combined organic phases were washed with brine (3×300 ml), water (300 ml) dried (Na2SO4) evaporated

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vigorously stirred solution of ethyl trans-3-(3-bromophenyl)-2-propenoate (26.71 g, 0.105 mol) in dry toluene (150 ml) at -5° C. (ice-EtOH) under nitrogen was treated with lithium aluminium hydride (3.98 g, 0.105 mol) in one portion. The reaction temperature was allowed to gradually warm to room temperature over 30 min., at 25° C. the reaction became quite exothermic (25°-40° C.) with the formation of a grey gelatinous precipitate. Stirring was continued for 1 h, after which the reaction was carefully quenched with water (300 ml) and ice (200 g) then allowed to stand at 25° C. for 30 min. The mixture was filtered through Celite (Registered Trade Mark) and the residue was washed with ethyl acetate (2×200 ml). The filtrate was extracted with the organic washings, the combined organic phases were washed with brine (3×300 ml), water (300 ml), dried (Na2SO4) and evaporated to give the title compound as a pale yellow oil (21.42 g, 96%). Distillation at 120° C. at 0.05 mmHg. gave a colourless oil. (Found C, 50.73; H, 4.12; Br, 37.53. C9H9BrO requires C, 50.73; H, 4.26; Br, 37.50%); νmax (thin film)/cm-1 3325.5 (br. OH), 2862.0, 1653.0, 1591.0, 1562.5; δH (270 MHz) 2.15 (1H, bs, 1-OH), 4.30 (2H, dd, 2×1-H, 3J1,2 =5.5, 4J1,3 1.5 Hz), 6.33 (1H, dt, 2-H, 3J2,3 =15.8, 3J2,1 =5.3 Hz), 6.53 (1H, dt, 3-H, 3J3,2 =16.2, 4J3,1 =1.3 Hz), 7.15 (1H, t, 5'-H, Jo =7.8 Hz), 7.26 (1H, dt, 6'-H, Jo =7.6, Jm =1.3 Hz), 7.35 (1H, dt, 4'-H, Jo =7.9, Jm =1.6 Hz), 7.50 (1H, t, 2'-H, Jm =1.6 Hz). δC (67.8 MHz) 63.2 (1-C), 122.7 (3'-C), 125.0 (2-C), 129.2 (5'-H), 138.8 (1'-C). The remaining signals fall in the narrow range 130.0 to 130.4 ppm; m/z 214.1, 212.1 (44.86,49.78, M+), 196.0, 194.0 (1.47, 1.03), 185.0, 183.0 (10.81, 12.19), 172.0, 170.0 (46.47, 49.07), 158.0, 156.0 (15.47, 15.80), 133.1, 131.1 (36.29, 25.66), 104.1 (100). (25°-40° C.) after which the reaction was carefully quenched with water (300 ml) and ice (200 g) to stand at 25° C. for 30 min The mixture was filtered through Celite (Registered Trade Mark) the residue was washed with ethyl acetate (2×200 ml) The filtrate was extracted with the organic washings the combined organic phases were washed with brine (3×300 ml), water (300 ml) dried (Na2SO4) evaporated

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

Procedure: A magnetically stirred solution of m-chloroperbenzoic acid (3.57 g, 10.33 mmol) in dichloromethane (60.0 ml) at 25° C. was treated dropwise with a solution of trans-3-(3-bromophenyl)-2-propenol (2.0 g, 9.39 mmol) in dichloromethane (20.0 ml). After stirring. for 16 h the mixture was diluted with dichloromethane (200 ml), washed with aqueous 1M NaOH (2×200 ml), brine (2×200 ml) and dried (Na2SO4). Evaporation of the solvent in vacuo returned the crude epoxide as a pale yellow oil (2.06 g). Column chromatography (ethyl acetate-light petroleum (b.p. 40-60° C.), 3:7) provided the title compound (1.53 g, 71%) as a pale yellow oil. washed with aqueous 1M NaOH (2×200 ml), brine (2×200 ml) dried (Na2SO4) Evaporation of the solvent in vacuo

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vigorously stirred solution of ethyl trans-3-(3-bromophenyl)-2-propenoate (26.71 g, 0.105 mol) in dry toluene (150 ml) at −5° C. (ice-EtOH) under nitrogen was treated with lithium aluminium hydride (3.98 g, 0.105 mol) in one portion. The reaction temperature was allowed to gradually warm to room temperature over 30 min., at 25° C. the reaction became quite exothermic (25-40° C.) with the formation of a grey gelatinous precipitate. Stirring was continued for 1 h, after which the reaction was carefully quenched with water (300 ml) and ice (200 g) then allowed to stand at 25° C. for 30 min. The mixture was filtered through Celite (Registered Trade Mark) and the residue was washed with ethyl acetate (2×200 ml). The filtrate was extracted with the organic washings, the combined organic phases were washed with brine (3×300 ml), water (300 ml), dried (Na2SO4) and evaporated to give the title compound as a pale yellow oil (21.42 g, 96%). Distillation at 120° C. at 0.05 mmHg. gave a colourless oil. (Found C, 50.73; H, 4.12; Br, 37.53. C9H9BrO requires C, 50.73; H, 4.26; Br, 37.50%); νmax (thin film)/cm−1 3325.5 (br. OH), 2862.0, 1653.0, 1591.0, 1562.5; δH (270 MHz) 2.15 (1H, bs, 1-OH), 4.30 (2H, dd, 2×1-H, 3J1,2=5.5, 4J1,3=1.5 Hz), 6.33 (1H, dt, 2-H, 3J2,3=15.8, 3J2,1=5.3 Hz), 6.53 (1H, dt, 3-H, 3J3,2=16.2, 4J3,1=1.3 Hz), 7.15 (1H, t, 5′-H, Jo=7.8 Hz), 7.26 (1H, dt, 6′-H, Jo=7.6, Jm=1.3 Hz), 7.35 (1H, dt, 4′-H, Jo=7.9, Jm=1.6 Hz), 7.50 (1H, t, 2′-H, Jm=1.6 Hz). δC (67.8 MHz) 63.2 (1-C), 122.7 (3′-C), 125.0 (2-C), 129.2 (5′-H), 138.8 (1′-C). The remaining signals fall in the narrow range 130.0 to 130.4 ppm; m/z 214.1, 212.1 (44.86,49.78, M+), 196.0, 194.0 (1.47, 1.03), 185.0, 183.0 (10.81, 12.19), 172.0, 170.0 (46.47, 49.07), 158.0, 156.0 (15.47, 15.80), 133.1, 131.1 (36.29, 25.66), 104.1 (100). (25-40° C.) after which the reaction was carefully quenched with water (300 ml) and ice (200 g) to stand at 25° C. for 30 min The mixture was filtered through Celite (Registered Trade Mark) the residue was washed with ethyl acetate (2×200 ml) The filtrate was extracted with the organic washings the combined organic phases were washed with brine (3×300 ml), water (300 ml) dried (Na2SO4) evaporated

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

Procedure: A magnetically stirred solution of m-chloroperbenzoic acid (3.57 g, 10.33 mmol) in dichloromethane (60.0 ml) at 25° C. was treated dropwise with a solution of trans-3-(3-bromophenyl)-2-propenol (2.0 g, 9.39 mmol) in dichloromethane (20.0 ml). After stirring for 16 h the mixture was diluted with dichloromethane (200 ml), washed with aqueous 1 M NaOH (2×200 ml), brine (2×200 ml) and dried (Na2SO4). Evaporation of the solvent in vacuo returned the crude eposide as a pale yellow oil (2.06 g). Column chromatography (ethyl acetate--light petroleum (b.p. 40-60° C.), 3:7) provided the title compound (1.53 g, 71%) as a pale yellow oil. washed with aqueous 1 M NaOH (2×200 ml), brine (2×200 ml) dried (Na2SO4) Evaporation of the solvent in vacuo

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

Procedure: The title compound was prepared from trans-3-(3-bromophenyl)-2-propenol by a sequence analogous to that described above for compound (9a) but using D-(-)-diethyl tartrate. Column chromatography (ethyl acetate--light petroleum (b.p. 40-60° C.), 3:7) provided the title compound (73%) as a pale yellow oil. Distilled at 160-185° C. at 0.1 mmHg. using a Kugelrohr short path distillation apparatus as a colourless oil; [α]D25 +37.6 (c=0.020 gml-1, CHCl3).

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vigorously stirred solution of ethyl trans-3-(3-bromophenyl)-2-propenoate (26.71 g, 0.105 mol) in dry toluene (150 ml) at -5° C. (ice-EtOH) under nitrogen was treated with lithium aluminium hydride (3.98 g, 0.105 mol) in one portion. The reaction temperature was allowed to gradually warm to room temperature over 30 min., at 25° C. the reaction became quite exothermic (25-40° C.) with the formation of a grey gelatinous precipitate. Stirring was continued for 1 h, after which the reaction was carefully quenched with water (300 ml) and ice (200 g) then allowed to stand at 25° C. for 30 min. The mixture was filtered through Celite (Registered Trade Mark) and the residue was washed with ethyl acetate (2×200 ml). The filtrate was extracted with the organic washings, the combined organic phases were washed with brine (3×300 ml), water (300 ml), dried (Na2SO4) and evaporated to give the title compound as a pale yellow oil (21.42 g, 96%). Distillation at 120° C. at 0.05 mmHg. gave a colourless oil. (Found C, 50.73; H, 4.12; Br, 37.53. C9H9BrO requires C, 50.73; H, 4.26; Br, 37.50%); Vmax (thin film)/cm-1 3325.5 (br. OH), 2862.0, 1653.0, 1591.0, 1562.5; δH (270 MHz) 2.15 (1H, bs, 1-OH), 4.30 (2H, dd, 2×1H, 3J1,2 =5.5, 4J1,3 =1.5 Hz), 6.33 (1H, dt, 2-H, 3J2,3 =15.8, 3J2,1 =5.3 Hz), 6.53 (1H, dt, 3-H, 3J3,2 =16.2, 4J3,1 =1.3 Hz), 7.15 (1H, t, 5'-H, Jo =7.8 Hz), 7.26 (1H, dt, 6'-H, Jo =7.6, Jm =1.3 Hz), 7.35 (1H, dt, 4'-H, Jo =7.9, Ja =1.6 Hz), 7.50 (1H, t, 2'-H, Jm =1.6 Hz). δC (67.8 MHz) 63.2 (1-C), 122.7 (3'-C), 125.0 (2-C), 129.2 95'-H), 138.8 (1'-C). The remaining signals fall in the narrow range 130.0 to 130.4 ppm; m/z 214.1, 212.1 (44.86,49.78, M+), 196.0, 194.0 (1.47, 1.03), 185.0, 183.0 (10.81, 12.19), 172.0, 170.0 (46.47, 49.07), 158.0, 156.0 (15.47, 15.80), 133.1, 131.1 (36.29, 25.66), 104.1 (100). (25-40° C.) after which the reaction was carefully quenched with water (300 ml) and ice (200 g) to stand at 25° C. for 30 min The mixture was filtered through Celite (Registered Trade Mark) the residue was washed with ethyl acetate (2×200 ml) The filtrate was extracted with the organic washings the combined organic phases were washed with brine (3×300 ml), water (300 ml) dried (Na2SO4) evaporated