Реакция #1610181

Уравнение реакции

NaH

Pentynol

BnBr

→

((pent-4-yn-1-yloxy)methyl)benzene

Выход 94.5%

Растворители

THF

Условия реакции

Обработка

1. 1
   ПромывкаThe solid was washed with hexanes (15 mL), THF (95 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   ТемператураThe reaction was warmed to ambient temperature over 16 h
4. 4
   Другоеquenched with saturated aqueous NH4Cl (25 mL)
5. 5
   workup.ADDITIONdiluted with water (20 mL)
6. 6
   ЭкстракцияThe organic layer was extracted with EtOAc (2×40 mL)
7. 7
   Промывкаwashed with brine (40 mL)
8. 8
   Сушкаdried with Na2SO4
9. 9
   КонцентрированиеProduct isolation was achieved by concentration in vacuo and purification by flash column chromatography

Методика

To a flame-dried round-bottomed flask was added NaH (2 equiv., 47.6 mmol, 1.9 g of a 60% dispersion in mineral oil). The solid was washed with hexanes (15 mL), THF (95 mL) was added and the suspension was cooled to 0° C. Pentynol (1 equiv., 23.8 mmol, 2.0 g) was added drop wise in THF (5 mL), followed by drop wise addition of BnBr (0.92 equiv., 21.9 mmol, 2.60 mL). The reaction was warmed to ambient temperature over 16 h, quenched with saturated aqueous NH4Cl (25 mL), and diluted with water (20 mL). The organic layer was extracted with EtOAc (2×40 mL), washed with brine (40 mL) and dried with Na2SO4. Product isolation was achieved by concentration in vacuo and purification by flash column chromatography to afford ((pent-4-yn-1-yloxy)methyl)benzene (3.60 g, 20.7 mmol, 94%). TLC Rf=0.41 (5% EtOAc/Hex); 1HNMR (300 MHz): δ 7.29-7.44 (5H), 4.55 (s, 2H), 3.61 (t, 2H, J=6.2 Hz), 2.36 (td, 2H, J=7.1, 2.6 Hz), 1.97 (t, 1H, J=2.6 Hz), 1.81-1.93 (m, 2H). 13CNMR (75 MHz): δ 138.5, 128.4, 127.63, 127.58, 84.0, 73.0, 68.7, 68.5, 28.7, 15.3.

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