Propargyl bromide → 678988-77-7

Temperature

-78 °C

To a solution of diisopropylamine (879 μL, 6.22 mmol) in anhydrous tetrahydrofuran (12 mL) at −40° C. under nitrogen was added 1.6 M n-butyl lithium in hexane (3.9 mL, 6.22 mmol), followed by hexamethylphosphoramide (4 mL). The mixture was cooled down to −78° C. and added a solution of methyl cyclohexanecarboxylate (80 7 μL, 5.65 mmol) tetrahydrofuran (4 mL) with the temperature maintained below −70° C. throughout the addition. After 15 min, propargyl bromide (80% w/w in xylene, 2.5 mL, 22.6 mmol) was added, and the reaction mixture was allowed to warm to room temperature. After 30 min, it was quenched with saturated ammonium chloride, and extracted with ethyl acetate. The organic phase was washed with water (×4), dried over MgSO4, filtered and concentrated to get 900 mg the title intermediate as a pale brown oil.

1. temperaturemaintained below −70° C. throughout the addition
2. temperatureto warm to room temperature
3. waitAfter 30 min
4. customit was quenched with saturated ammonium chloride
5. extractionextracted with ethyl acetate
6. washThe organic phase was washed with water (×4)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-3b3efc8a83134582a7ba2ca8f5666ccd

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557828B2