反应 #2171070

反应方程式

HCl

tetraethylene glycol

sodium

tert-butyl acrylate

→

product 9a

收率 73.0%

15-Hydroxy-4,7,10,13-tetraoxapentadecanoic Acid tert-Butyl Ester

收率 73.0%

溶剂

THF

反应条件

后处理

1. 1
   其他The solvent was removed in vacuo
2. 2
   萃取extracted with ethyl acetate (3×125 mL)
3. 3
   洗涤The combined organic layers were washed with brine (100 mL)
4. 4
   干燥water (100 mL), dried over sodium sulfate
5. 5
   其他the solvent was removed
6. 6
   其他The resulting colorless oil was dried under vacuum

实验过程

To 300 mL of anhydrous THF was added 80 mg (0.0025 mol) of sodium metal and 128 mL of tetraethylene glycol 4a (0.94 mol) with stirring (Seitz and Kunz, J. Org. Chem., 62:813-826 (1997)). After the sodium had completely dissolved, tert-butyl acrylate (24 mL, 0.33 mol) was added. The solution was stirred for 20 hrs at room temperature and neutralized with 8 mL of 1.0 M HCl. The solvent was removed in vacuo and the residue was suspended in brine (250 mL) and extracted with ethyl acetate (3×125 mL). The combined organic layers were washed with brine (100 mL) then water (100 mL), dried over sodium sulfate, and the solvent was removed. The resulting colorless oil was dried under vacuum to give 77.13 g (73% yield) of product 9a (FIG. 7). 1H NMR: 1.40 (s, 9H), 2.49 (t, 2H, J=6.4 Hz), 3.59-3.73 (m, 18H).

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