Diethyl Ether → 4-(2,2-Dimethoxyethyl)hepta-1,6-dien-4-ol

온도

-78 °C

In a 2 liter round bottom flask equipped with a stir bar, methyl 3,3-dimethoxypropanoate (24 g, 162 mmol) was dissolved in THF (1L). Under nitrogen, the solution was chilled to −78° C. Allyl Magnesium bromide, 1.0 M solution in diethyl ether (405 mL, 405 mmol) was added dropwise in such a way that the internal temperature remained lower than −75° C. After addition, the reaction was allowed to stir for 3 hours at −78° C. before being quenched with saturated ammonium chloride solution (300 mL). The ice bath was removed and the reaction allowed to come to RT. Water was added (200 mL) and the reaction was concentrated on a rotary evaporator to remove as much THF as possible. The product was extracted from the resulting aqueous with diethyl ether (3×200 mL). The organics were then washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated to afford the product.

1. customIn a 2 liter round bottom flask equipped with a stir bar
2. customremained lower than −75° C
3. additionAfter addition
4. custombefore being quenched with saturated ammonium chloride solution (300 mL)
5. customThe ice bath was removed
6. customto come to RT
7. additionWater was added (200 mL)
8. concentrationthe reaction was concentrated on a rotary evaporator
9. customto remove as much THF as possible
10. extractionThe product was extracted from the resulting aqueous with diethyl ether (3×200 mL)
11. washThe organics were then washed with brine (100 mL)
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated
15. customto afford the product

ORD 기록

ord-469e7e67a98446b0a6374337acf6a7f4

출처 데이터셋

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07745484B2