تفاعل #6678

ord-042ea76dc6784c55b2a71fe62bfbe739

معادلة التفاعل

CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C=Cc4cc(C=O)cc(C=Cc5cc(C=Cc6cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)c6)cc(C=Cc6cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)c6)c5)c4)cc(C=Cc4cc(C=Cc5cc(C(C)(C)C)cc(C(C)(C)C)c5)cc(C=Cc5cc(C(C)(C)C)cc(C(C)(C)C)c5)c4)c3)cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)c2)cc(C(C)(C)C)c1
3,5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzaldehyde
[BH4-].[Na+]
sodium borohydride
→
CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C=Cc4cc(C=Cc5cc(C(C)(C)C)cc(C(C)(C)C)c5)cc(C=Cc5cc(C(C)(C)C)cc(C(C)(C)C)c5)c4)cc(C=Cc4cc(C=Cc5cc(C=Cc6cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)c6)cc(C=Cc6cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)c6)c5)cc(CO)c4)c3)cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)c2)cc(C(C)(C)C)c1
3,5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzyl alcohol
المردود 80.0%

المتفاعلات

CC(C)(C)c1cc(C=Cc2cc(C=Cc3cc(C=Cc4cc(C=O)cc(C=Cc5cc(C=Cc6cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)c6)cc(C=Cc6cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)cc(C=Cc7cc(C(C)(C)C)cc(C(C)(C)C)c7)c6)c5)c4)cc(C=Cc4cc(C=Cc5cc(C(C)(C)C)cc(C(C)(C)C)c5)cc(C=Cc5cc(C(C)(C)C)cc(C(C)(C)C)c5)c4)c3)cc(C=Cc3cc(C(C)(C)C)cc(C(C)(C)C)c3)c2)cc(C(C)(C)C)c1
3,5-bis{3′,5′-bis[3″,5″-bis(3′″,5′″-di-tert-butylstyryl)styryl]styryl}benzaldehyde
[BH4-].[Na+]
sodium borohydride

الكواشف

لا شيء

المذيبات

C1CCOC1
tetrahydrofuran

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةheated
  2. 2
    درجة الحرارةat reflux for 135 min
  3. 3
    أخرىThe solvent was removed
  4. 4
    workup.ADDITIONDichloromethane (50 cm3) was added
  5. 5
    غسيلthe solution washed with water (50 cm3) and brine (50 cm3)
  6. 6
    تجفيفdried over sodium sulphate
  7. 7
    ترشيحfiltered
  8. 8
    أخرىthe solvent removed
  9. 9
    أخرىto leave a yellow foam
  10. 10
    أخرىThe product was purified by column chromatography over silica
  11. 11
    غسيلeluting with dichloromethane-light petroleum (2:3)
  12. 12
    أخرىRecrystallisation from a dichloromethane-methanol mixture

الإجراء التجريبي

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%); vmax(KBr)/cm−1 3568 (OH), 1594 (C═C) and 959 (C═C—H trans); λmax(CH2Cl2)/nm (log ε) 323 (5.59) and 334sh (5.52); δH(400 MHz, CDCl3) 1.39 (144H, s, t-Bu), 1.80 (1H, t, OH), 4.85 (2H, d, CH2OH), 7.19 and 7.31 (16H, ABq, J 16, 7′″, 8′″-H), 7.32(4H, s, 7′, 8′-H), 7.34(8H, s, 7″, 8″-H), 7.38 (8H, dd, J 1.5, 4′″-H), 7.44 (16H, d, J 1.5, 2′″, 6′″-H), 7.57(2H, br s, 4′-H), 7.67 (12H, br s, 2″, 4″, 6″-H), 7.67 (4H, br s, 2′, 6′-H), 7.70 (1H, br s, 4-H) and 7.74 (2H, br s, 2, 6-H); m/z (MALDI) 2434.94 (M+, 100%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07083862B2uspto-grants-2006_08