[1-(2-Oxoethyl)cyclopropyl]acetonitrile → [1-(2-Hydroxypropyl)cyclopropyl]acetonitrile
Reaction equation
[O:1]=[CH:2][CH2:3][C:4]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5]1.[CH3:10][Mg]Cl>C1COCC1>[OH:1][CH:2]([CH3:10])[CH2:3][C:4]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a -5° C. solution of the aldehyde from Step 2 (3.00 g, 24.4 mmol) in 65 mL of THF was added methyl magnesium chloride (3.0M solution in THF, 9.5 mL, 29 mmol) and the reaction was stirred 2 h at 0° C. The reaction was quenched with 1M HCl and extracted with ethyl acetate. The organic extracts were washed with saturated NaHCO3 and brine and dried over MgSO4. Purification by flash chromatography (30% ethyl acetate/hexanes) provided 2.46 g of the title product.
Workup
- customThe reaction was quenched with 1M HCl
- extractionextracted with ethyl acetate
- washThe organic extracts were washed with saturated NaHCO3 and brine
- dry with materialdried over MgSO4
- customPurification by flash chromatography (30% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-a7bfc9dfccc74fdd926ebaabd6a5c5b2
- Source dataset
- uspto-grants-1997_06
- Patent number
- US05639780
Reaction notes
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