Propargyl bromide → HCID 11506529, compound

To a suspension of sodium hydride (60% dispersion in mineral oil) (23 mmol) in dry THF (10 mL) at 0° C. under nitrogen was gradually added terButylglycolate (19.1 mmol). The resultant reaction mixture was allowed to stir at room temperature for 30 min. This was followed by the addition of Propargyl bromide (23 mmol). The reaction mixture was then stirred at room temperature for 8 h. The reaction was concentrated in vacuo and diluted with water (30 mL). The mixture was then extracted with DCM (3×). The organics were combined, dried over sodium sulfate, filtered and concentrated under vacuum to furnish a crude residue. This was subjected to flash column chromatography using hexanes and ethyl acetate to afford 19 as a clear oil (70% yield).

1. customThe resultant reaction mixture
2. stirringThe reaction mixture was then stirred at room temperature for 8 h
3. concentrationThe reaction was concentrated in vacuo
4. additiondiluted with water (30 mL)
5. extractionThe mixture was then extracted with DCM (3×)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customto furnish a crude residue

ORD record

ord-366442920db7489bbb9ca7ed05c33d3e

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461171B2