Propargyl bromide → 1-(1-Propylcyclobutyl)but-3-yn-1-ol

Temperature

40 °C

Propargyl bromide (0.27 mL, 2.4 mmol) was added to a mixture of magnesium (1.1 g, 45 mmol) and mercuric chloride (30 mg, 0.117 mmol) in Et2O (60 mL). The mixture was warmed to 40° C. until bubbling commenced. The remainder of the propargyl bromide (2.1 mL, 19 mmol) was added in small portions. After −1.5 h the reaction became cloudy white. A solution of the aldehyde 3 (0.8 g, 7 mmol) in Et2O (4 mL) was added and the reaction was stirred for 16 h. The reaction was then quenched by cautiously adding saturated aqueous NH4Cl. The resultant mixture was extracted with Et2O. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 1:1 pentane/CH2Cl2) gave 1.0 g (94%) of the alcohol 4.

1. customuntil bubbling
2. waitAfter −1.5 h the reaction became cloudy
3. customThe reaction was then quenched by cautiously adding saturated aqueous NH4Cl
4. extractionThe resultant mixture was extracted with Et2O
5. washThe organic portion was washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-81a15a3e8ff14f9bb438663efb15bd24

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07314890B2