Реакция #425668

Уравнение реакции

N2

HCl

3-iodotetrahydrofuran

N2

4-bromophenylboronic acid

sodium hexamethyldisilazide

trans-2-aminocyclohexanol

→

title compound

(±)-3-(4-Bromophenyl)tetrahydrofuran

Растворители

i-PrOH

i-PrOH

Условия реакции

Обработка

1. 1
   Другоеwas sealed in a microwave vial
2. 2
   Другоеirradiation at 80° C. for 20 minutes
3. 3
   ДругоеThe cooled reaction mixture
4. 4
   Экстракцияextracted with heptane/EtOAc (2:1, 3×20 mL)
5. 5
   СушкаThe combined organic layers were dried over Na2SO4
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   Другоеto give a yellow solid
8. 8
   ДругоеThe crude material was purified by flash chromatography (0-5% EtOAc/Heptane)

Методика

A mixture of 4-bromophenylboronic acid (1.7 g, 8.1 mmol), nickel iodide (102 mg, 0.32 mmol), solid sodium hexamethyldisilazide (1.6 g, 8.1 mmol) and trans-2-aminocyclohexanol (49.0 mg, 0.32 mmol) was sealed in a microwave vial, diluted with dry i-PrOH (7 mL), and evacuated/backfilled with N2 three times. The reaction mixture was stirred at room temperature for 5 minutes, treated with a solution of 3-iodotetrahydrofuran (800 mg, 4.04 mmol) in i-PrOH (1 mL) and evacuated/backfilled with N2. The reaction mixture was subjected to microwave irradiation at 80° C. for 20 minutes. The cooled reaction mixture was poured into 0.3N HCl (30 mL) and extracted with heptane/EtOAc (2:1, 3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give a yellow solid. The crude material was purified by flash chromatography (0-5% EtOAc/Heptane) to give the title compound (471 mg, 51% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=8.39 Hz, 2H), 7.11 (d, J=8.39 Hz, 2H), 4.09 (t, J=8.00 Hz, 1H), 4.04 (td, J=8.39, 4.69 Hz, 1H), 3.89 (q, J=8.00 Hz, 1H), 3.65-3.70 (m, 1H), 3.34 (quin, J=7.66 Hz, 1H), 2.35 (dtd, J=12.37, 7.77, 7.77, 4.68 Hz, 1H), 1.94 (dq, J=12.37, 8.04 Hz, 1H).

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