تفاعل #1857553

معادلة التفاعل

benzyl bromide

(3S,4R)-4-((S)-1-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-1-en-3-ol

NaH

→

title compound

المردود 91.0%

1-((((2S,3S)-3-((S)-1-(benzyloxy)allyl)-6-methylheptan-2-yl)oxy)methyl)-4-methoxybenzene

المردود 91.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwarmed to 45° C.
2. 2
   workup.STIRRINGstirred at this temperature for 16 h
3. 3
   درجة الحرارةThe reaction was cooled to room temperature
4. 4
   أخرىquenched with sat. aq. NH4Cl (40 mL)
5. 5
   استخلاصThe mixture was extracted with Et2O (3×50 mL)
6. 6
   غسيلthe combined organics were washed with brine (40 mL)
7. 7
   تجفيفdried over Na2SO4
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated to dryness
10. 10
    أخرىThe residue was purified

الإجراء التجريبي

To a solution of (3S,4R)-4-((S)-1-((4-methoxybenzyl)oxy)ethyl)-7-methyloct-1-en-3-ol (2.34 g, 7.64 mmol) in DMF (15.3 mL) was added NaH (0.611 g, 15.3 mmol, 60% dispersion in mineral oil) at 0° C. After 20 min, benzyl bromide (2.27 mL, 19.1 mmol) was added and the reaction was stirred at 0° C. for 20 min, warmed to 45° C., and stirred at this temperature for 16 h. The reaction was cooled to room temperature and quenched with sat. aq. NH4Cl (40 mL). The mixture was extracted with Et2O (3×50 mL), and the combined organics were washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated to dryness. The residue was purified using flash column chromatography (120 g SiO2, 0→20% EtOAc/hexanes) to afford the title compound (2.75 g, 6.93 mmol, 91%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.38-7.34 (m, 2H), 7.32-7.25 (m, 3H), 7.22-7.17 (m, 2H), 6.87-6.78 (m, 2H), 5.78 (ddd, J=17.4, 9.9, 7.3 Hz, 1H), 5.27-5.18 (m, 2H), 4.58 (d, J=12.4 Hz, 1H), 4.42 (d, J=11.2 Hz, 1H), 4.29 (d, J=11.2 Hz, 1H), 4.26 (d, J=11.9 Hz, 1H), 4.04-3.96 (m, 1H), 3.77 (s, 3H), 3.64 (p, J=6.3 Hz, 1H), 1.73-1.63 (m, 1H), 1.55-1.42 (m, 2H), 1.43-1.21 (m, 3H), 1.15 (d, J=6.3 Hz, 3H), 0.86 (d, J=6.6 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 158.92, 139.07, 137.94, 131.19, 129.17, 128.19, 127.77, 127.47, 116.82, 113.65, 81.13, 75.03, 70.36, 70.07, 55.22, 48.17, 38.66, 28.62, 23.67, 22.61, 16.84; ESIMS m/z 419 ([M+Na]+).

المصدر