Diisopropylamine → HCID 13358204, compound

Temperature

0 °C

To a solution of diisopropylamine (654 mg, 6.46 mmol) in anhydrous tetrahydrofuran (5 mL) under the atmosphere of argon was added a 1.58 M n-butyl lithium-hexane solution (3.9 mL, 6.4 mmol) with stirring under ice cooling, and the mixture was stirred at 0° C. for 10 min and at −90° C. for 5 min. To the mixture, a solution of ethyl 2-bromo-n-butyrate (1.00 g, 5.13 mmol) in anhydrous tetrahydrofuran (9.5 mL) was added dropwise at −90° C., and the mixture was stirred for 30 min. Copper (I) iodide (489 mg, 2.56 mmol) was added at the same temperature, and the mixture was vigorously stirred further 5 min. The temperature was raised to 0° C. with stirring, and a saturated aqueous ammonium chloride solution (30 mL) was added. The reaction mixture was directly filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted twice with ethyl acetate, and the combined organic layer was washed sequentially with water and brine and concentrated. The residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 9:1) to give 368.4 mg of the title compound as oil (yield: 63%).

1. stirringthe mixture was stirred at 0° C. for 10 min and at −90° C. for 5 min
2. stirringthe mixture was stirred for 30 min
3. stirringwith stirring
4. filtrationThe reaction mixture was directly filtered
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionThe residue was diluted with water
7. extractionextracted twice with ethyl acetate
8. washthe combined organic layer was washed sequentially with water and brine
9. concentrationconcentrated
10. customThe residue thus obtained

ORD record

ord-fac7af51323c4bcc9d754e88726a5b2e

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260375B2