反応 #1265358
ord-875971bea7724064a70462a638693ad8
反応方程式
反応物
試薬
反応条件
後処理
- 1温度heated
- 2温度at reflux for 135 min
- 3その他The solvent was removed
- 4workup.ADDITIONDichloromethane (50 cm3) was added
- 5洗浄the solution washed with water (50 cm3) and brine (50 cm3)
- 6乾燥dried over sodium sulphate
- 7ろ過filtered
- 8その他the solvent removed
- 9その他to leave a yellow foam
- 10その他The product was purified by column chromatography over silica
- 11洗浄eluting with dichloromethane-light petroleum (2:3)
- 12その他Recrystallisation from a dichloromethane-methanol mixture
実験手順
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%).