Triethylamine → HCID 86590501, compound

Temperature

0 °C

1-Bromopropan-3-ol (1.32 mL, 14.6 mmol) was dissolved in anhydrous methylene chloride and cooled to 0° C. under nitrogen atmosphere. The solution was treated with triethylamine (2.2 mL, 15.8 mmol) and methoxyacetyl chloride (1.42 mL, 15.5 mmol) then warmed to room temperature. The reaction mixture was stirred for 17.5 h. It was then diluted with methylene chloride (150 mL) and extracted with saturated sodium bicarbonate (2×50 mL). The aqueous phase was back extracted with methylene chloride (100 mL) and the organic phases were combined and concentrated in vacuo to yield a crude, pale yellow oil (3.27 g). 1H NMR δ 4.25 (t, 2H, J=6.1), 4.05 (s, 2H), 3.45 (s, 3H), 3.22 (t, 2H, I=6.9), 2.18 (quint, 2H, J=6.6). The product was used as such in the following reaction.

1. temperaturethen warmed to room temperature
2. extractionextracted with saturated sodium bicarbonate (2×50 mL)
3. extractionThe aqueous phase was back extracted with methylene chloride (100 mL)
4. concentrationconcentrated in vacuo

ORD record

ord-1cc0529a85f04dd4a35240c097733ba4

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439264B2