Tetrahydrofuran → 3,6,9,12-Tetraoxapentadec-14-en-1-ol

Temperature

0 °C

Under nitrogen atmosphere, NaH (1.2 g, 50 mmol) was charged into a flask, and then dry THF (15 mL) was added thereto and stirred at 0° C. for 15 minutes. Tetraethyleneglycol (10.7 g, 55 mmol) was added to the NaH mixture at 0° C. The mixture was stirred at room temperature for 1 hour. Next, the mixture was diluted with water (20 mL) and an organic material was extracted with methylene chloride (3×10 mL). The resulting organic layer was collected, dried on MgSO4 and concentrated to obtain a crude product as yellow liquid. The crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH)) to obtain the target product (3.8 g, 32%) in a colorless oily phase. The NMR analysis result of the obtained product is as follows.

1. stirringThe mixture was stirred at room temperature for 1 hour
2. extractionan organic material was extracted with methylene chloride (3×10 mL)
3. customThe resulting organic layer was collected
4. customdried on MgSO4
5. concentrationconcentrated
6. customto obtain a crude product as yellow liquid
7. customThe crude product was purified with a column chromatography (Hex:EA=1:2 (10% MeOH))

ORD record

ord-b49584be25f64cbbba8f7e4dc000af2a

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718577B2