Réaction #1265358

Équation de réaction

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

Rendement 80.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températureheated
2. 2
   Températureat reflux for 135 min
3. 3
   AutreThe solvent was removed
4. 4
   workup.ADDITIONDichloromethane (50 cm3) was added
5. 5
   Lavagethe solution washed with water (50 cm3) and brine (50 cm3)
6. 6
   Séchagedried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Autrethe solvent removed
9. 9
   Autreto leave a yellow foam
10. 10
    AutreThe product was purified by column chromatography over silica
11. 11
    Lavageeluting with dichloromethane-light petroleum (2:3)
12. 12
    AutreRecrystallisation from a dichloromethane-methanol mixture

Mode opératoire

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%).

Source