1,3-Dibromopropane → HCID 10801356, compound

Temperature

-10 °C

Under argon flow, 13.46 g of 3-(tetrahydro-2H-pyran-2-yloxy)-1-propyne was dissolved in 135 ml of anhydrous tetrahydrofuran, and 60 ml of 1.6 N n-butyllithium hexane solution was added dropwise over 20 minutes with stirring at −10° C. of inner temperature. The mixture was stirred for 1 hour at the same temperature. After stirring for additional 1 hour at room temperature, the inner temperature was changed to −3° C., and 16.7 ml of hexamethylphosphoric triamide (HMPA) was added to the mixture. Then 58.14 g of 1,3-dibromopropane was added in a portion at −10° C. of inner temperature, and the mixture was stirred for 12 hours at room temperature. The reaction solution was poured into ice-cold water, extracted with ether, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was distilled under reduced pressure to give 12.0 g of the objective compound as colorless oil.

1. stirringThe mixture was stirred for 1 hour at the same temperature
2. stirringAfter stirring for additional 1 hour at room temperature
3. customwas changed to −3° C.
4. stirringthe mixture was stirred for 12 hours at room temperature
5. additionThe reaction solution was poured into ice-cold water
6. extractionextracted with ether
7. washwashed with water
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated
10. distillationThe residue was distilled under reduced pressure

ORD record

ord-2c2b14307852483088cc11a4e312d655

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06998412B2