Methyl 1-methylcyclopropyl ketone → 2-(1-Methylcyclopropyl)but-3-yn-2-ol

Temperature

0 °C

This compound was prepared according to a procedure similar to that described in Procedure A. In a 100-mL 3-necked round-bottom flask, a solution of 1-(1-methylcyclopropyl)ethan-1-one (2 g, 20.38 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) was added into a solution of bromo(ethynyl)magnesium (0.5 M in THF, 53 mL, 1.30 equiv) in tetrahydrofuran (5 mL). The resulting solution was stirred for 8 h at 0° C. in an ice/salt bath. The reaction was then quenched by the addition of 50 mL of sat. aq. NH4Cl. The resulting solution was extracted with 3×150 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×150 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 120 mg (5%) of 2-(1-methylcyclopropyl)but-3-yn-2-ol as colorless oil.

1. customThis compound was prepared
2. customThe reaction was then quenched by the addition of 50 mL of sat. aq. NH4Cl
3. extractionThe resulting solution was extracted with 3×150 mL of ethyl acetate
4. washThe resulting mixture was washed with 3×150 mL of brine
5. dry with materialThe mixture was dried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. customThis resulted in 120 mg (5%) of 2-(1-methylcyclopropyl)but-3-yn-2-ol as colorless oil

ORD record

ord-7a8aaa9e5eb948379e0d55f0734428ef

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034866B2