反应 #1702034

反应方程式

HCl

diisopropylethylamine

acetyl bromide

5

3-Methoxydodecanal

AlMe3

→

6

收率 77.3%

(4R)-4-((2RS)-2-Methoxyundecyl)oxetan-2-one

收率 77.3%

溶剂

CH2Cl2

CH2Cl2

反应条件

后处理

1. 1
   温度cooled to −45° C.
2. 2
   workup.STIRRINGThe resulting pale yellow solution was stirred for 14 h at −45° C.
3. 3
   温度warmed to rt
4. 4
   workup.ADDITIONpoured into a separatory funnel
5. 5
   洗涤The organic layer was washed with saturated NaHCO3, brine
6. 6
   干燥dried (Na2SO4)
7. 7
   其他The solvent was removed in vacuo
8. 8
   其他the yellow oily product was purified by chromatography on SiO2 (4% EtOAc/hexanes to 6% EtOAc/hexanes)

实验过程

A solution of N,N′-(1R,1′R)-1,1′-(benzylazanediyl)bis(2-methylpropane-1,1-diyl)bis(1,1,1-trifluoromethanesulfonamide) (81.2 mg, 0.15 mmol, 30 mol %) in CH2Cl2 (1 mL) was treated at rt under N2 slowly with a solution of AlMe3 (10.8 mg, 0.15 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred at room temperature (rt) for 2 h, cooled to −45° C. and treated sequentially with diisopropylethylamine (11 mg, 1.7 equiv), acetyl bromide (117 mg, 1.9 equiv) and 5 (107 mg, 0.500 mmol, 1.0 equiv). The resulting pale yellow solution was stirred for 14 h at −45° C., warmed to rt, and poured into a separatory funnel containing 0.1 N HCl (10) mL). The organic layer was washed with saturated NaHCO3, brine, and dried (Na2SO4). The solvent was removed in vacuo and the yellow oily product was purified by chromatography on SiO2 (4% EtOAc/hexanes to 6% EtOAc/hexanes) to give 6 (99.1 mg, 77%) as a colorless oil: 1H NMR (CDCl3) 4.8-4.65 (m, 1H), 3.60-3.50 (m, 1H), 3.3-3.2 (m, 1H), 3.35, 3.32 (2s, 3H), 3.22-3.08 (m, 1H), 2.18-1.82 (m, 2H) 1.65-1.35 (m, 2H), 1.35-1.20 (m, 14H), 0.90-0.80 (m, 3H).

来源