Reaktion #1265358

Reaktionsgleichung

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

Ausbeute 80.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux for 135 min
3. 3
   SonstigeThe solvent was removed
4. 4
   workup.ADDITIONDichloromethane (50 cm3) was added
5. 5
   Waschenthe solution washed with water (50 cm3) and brine (50 cm3)
6. 6
   Trocknendried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvent removed
9. 9
   Sonstigeto leave a yellow foam
10. 10
    SonstigeThe product was purified by column chromatography over silica
11. 11
    Wascheneluting with dichloromethane-light petroleum (2:3)
12. 12
    SonstigeRecrystallisation from a dichloromethane-methanol mixture

Vorschrift

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%).

Quelle