Dimethylamine → HCID 45087887, compound

Prop-2-ynyloxyacetyl chloride (1.74 g) in tetrahydrofuran (20 ml) was added dropwise over 5 min. to a stirred solution of dimethylamine (12 ml of 33% solution in ethanol) in tetrahydrofuran (15 ml) at ambient temperature. After 30 minutes the solvent was evaporated and the residue was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ethyl acetate (30 ml). The aqueous layer was separated and then re-extracted with ethyl acetate (20 ml). The combined ethyl acetate extracts were washed with brine (20 ml), dried over sodium sulphate and then evaporated. There was thus obtained the title compound as a liquid (1.15 g). NMR Spectrum: (CDCl3) 2.47 (t, 1H), 2.96 (s, 3H), 3.02 (s, 3H), 4.27 (s, 2H), 4.33 (d, 2M); Mass Spectrum: M+H+ 142.

1. customAfter 30 minutes the solvent was evaporated
2. customthe residue was partitioned between saturated aqueous sodium bicarbonate (20 ml) and ethyl acetate (30 ml)
3. customThe aqueous layer was separated
4. extractionre-extracted with ethyl acetate (20 ml)
5. washThe combined ethyl acetate extracts were washed with brine (20 ml)
6. dry with materialdried over sodium sulphate
7. customevaporated

ORD record

ord-f77a65b8fc344d2fada7b2f3d4e3e5ad

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504408B2