반응 #2033

반응 방정식

triphenylphosphine

Br2

4,7-decadien-1-ol

NaHCO3

→

(4Z,7Z)-1-bromo-4,7-decadiene

수율 32.0%

용매

CH2Cl2

CH2Cl2

CH2Cl2

water

반응 조건

후처리

1. 1
   기타Into the slightly yellow suspension that formed
2. 2
   workup.ADDITIONthe crude mixture of 4
3. 3
   workup.STIRRINGAfter stirring for 1 hour
4. 4
   추출The mixture was extracted with pentane
5. 5
   workup.WAITwere stored overnight in a freezer
6. 6
   기타In this way, triphenylphosphine oxide could be crystallized
7. 7
   기타removed by filtration
8. 8
   workup.DISTILLATIONColumn chromatography followed by distillation at reduced pressure
9. 9
   기타afforded 5 (3.48 g, 32% yield
10. 10
    기타=80°-85° C./2.5 torr

실험 절차

A solution of triphenylphosphine (20.9 g, 80 mmol) in CH2Cl2 (100 ml) was treated with Br2 (7.8 g, 49 mmol) in CH2Cl2 (15 mL, 0° C.) and the mixture was stirred at room temperature for 20 min. Into the slightly yellow suspension that formed, the crude mixture of 4 and 4Z,7Z)-4,7-decadien-1-ol (12.4 g) in CH2Cl2 (15 ml) was added dropwise. After stirring for 1 hour, a solution of saturated NaHCO3 (50 mL) and water (50 ml) were added. The mixture was extracted with pentane and combined extracts were stored overnight in a freezer. In this way, triphenylphosphine oxide could be crystallized and removed by filtration. Column chromatography followed by distillation at reduced pressure afforded 5 (3.48 g, 32% yield based on 1 of b.p. =80°-85° C./2.5 torr. 1H NMR (200 MHz) δ: 5.37 (m, 4H, CH=CH), 3.41 (t, J=6.6, 6.6 Hz, 2H, CH2 --Br), 2.80 (dd, J=6.4, 6.5 Hz, 2H, =CH--CH2 --CH=), 2.21 (dt, J=7.0, 6.9, 6.8, 6.9 Hz, 2H, CH2 -3), 2.07 (dq, J=7.4 Hz, CH2 -9), 1.91 (tt, J=6.7, 6.6, 7.0, 7.0, 2H, CH2 -2), 0.97 (t, J=7.5, 7.5 Hz, 3H, CH3). 13C NMR (100.6 MHz) δ: 132.1 (8), 129.8 (5), 127.6 (7), 127.0 (4), 33.4 (1), 32.5 (2), 25.6 (3), 25.5 (6), 20.6 (9), 14.3 (10). MS [EI, m/z (%)] 218 (M+, 15), 216 (17), 137 (6), 109 (13), 107 (18), 96 (14), 95 (78), 82 (18), 81 (74), 79 (22), 68 (27), 67 (100), 55 (17), 53 (15), 42 (11), 41 (38), 40 (40).

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