Triethylamine → HCID 54382309, compound

Temperature

0 °C

4-Pentenoyl chloride (2.8 mL, 25.4 mmol) was dissolved in anhydrous methylene chloride (50 mL) and cooled to 0° C. under nitrogen. 2-Bromoethanol (2.0 mL, 28.2 mmol) and triethylamine (3.8 mL, 27.3 mmol) was added to the reaction solution resulting in a thick yellow slurry. The reaction solution was stirred for 19.5 h while slowly warming to 22° C. The reaction mixture was diluted to 100 mL with methylene chloride and extracted with 75 mL of each of the following: water, sat. ammonium chloride, and sat. sodium bicarbonate. The organic phase was dried (MgSO4), filtered and condensed in vacuo to yield a yellow oil (5.2 g cu. 100%) which was used as is for the next step. 1H NMR δ 5.90-5.65 (m, I H), 5.15-4.90 (m, 2H), 4.39 (t, 2H, J=6.0), 3.48 (t, 2H, J=6.0), 2.50-2.30 (m, 4H).

1. customresulting in a thick yellow slurry
2. temperaturewhile slowly warming to 22° C
3. extractionextracted with 75 mL of each of the following: water, sat. ammonium chloride, and sat. sodium bicarbonate
4. dry with materialThe organic phase was dried (MgSO4)
5. filtrationfiltered
6. customcondensed in vacuo
7. customto yield a yellow oil (5.2 g cu. 100%) which

ORD record

ord-403fdbd52dd1469c92ca182017785816

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439264B2