Реакция #1265358

Уравнение реакции

3,5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzaldehyde

sodium borohydride

→

3, 5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzyl alcohol

Выход 80.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураheated
2. 2
   Температураat reflux for 135 min
3. 3
   ДругоеThe solvent was removed
4. 4
   workup.ADDITIONDichloromethane (50 cm3) was added
5. 5
   Промывкаthe solution washed with water (50 cm3) and brine (50 cm3)
6. 6
   Сушкаdried over sodium sulphate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеthe solvent removed
9. 9
   Другоеto leave a yellow foam
10. 10
    ДругоеThe product was purified by column chromatography over silica
11. 11
    Промывкаeluting with dichloromethane-light petroleum (2:3)
12. 12
    ДругоеRecrystallisation from a dichloromethane-methanol mixture

Методика

A solution of 3,5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzaldehyde (3.853 g, 1.585 mmol) in tetrahydrofuran (50 cm3) was treated with sodium borohydride (121 mg, 3.20 mmol) and heated at reflux for 135 min. The solvent was removed. Dichloromethane (50 cm3) was added and the solution washed with water (50 cm3) and brine (50 cm3), dried over sodium sulphate, filtered and the solvent removed to leave a yellow foam. The product was purified by column chromatography over silica, eluting with dichloromethane-light petroleum (2:3). Recrystallisation from a dichloromethane-methanol mixture gave 3, 5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzyl alcohol (3.07 g, 80%) as a yellow powder, mp 248° C. (Found: C, 89.89; H, 8.89. C183H220O requires C, 90.24; H, 9.10%); νmax(KBr)/cm−1 3568 (OH), 1594 (C═C) and 959 (C═C—H trans); λmax(CH2Cl2)/nm (logε) 323 (5.59) and 334 sh (5.52); δH(400 MHz, CDCl3) 1.39 (144 H, s, t-Bu), 1.80 (1H, t, OH), 4.85 (2 H, d, CH2OH), 7.19 and 7.31 (16 H, ABq, J 16, 7′″,8′″-H), 7.32 (4 H, s, 7′,8′-H), 7.34 (8 H, s, 7″, 8″-H), 7.38(8 H, dd, J 1.5, 4′″-H), 7.44 (16 H, d, J 1.5, 2′″,6′″-H), 7.57 (2 H, br s, 4′-H), 7.67(12 H, br s, 2″,4″,6″-H), 7.67 (4 H, br s, 2′,6′-H), 7.70 (1 H, br s, 4-H) and 7.74 (2 H, br s, 2,6-H); m/z (MALDI) 2434.94 (M+, 100%).

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