Acetonitrile → 3-(1-Hydroxymethyl-cyclopropyl)-3-oxo-propionitrile
Reaction equation
[Li+].[CH3:2][CH:3]([N-:5]C(C)C)C.C[O:10][C:11]([C:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1)=O.CC#N>C1COCC1>[OH:17][CH2:16][C:13]1([C:11](=[O:10])[CH2:2][C:3]#[N:5])[CH2:15][CH2:14]1Participants
5
Procedure
To a solution of LDA (115 mmol) in THF (300 mL), at −78° C., a solution of 1-hydroxymethyl-cyclopropanecarboxylic acid methyl ester (5 g, 28.4 mmol) in CH3CN (5.91 mL, 115 mmol) is added. The reaction is allowed to reach rt. At this point it is quenched with 1N HCl (200 mL) and extracted with EtOAc (200 mL, ×3). It is then dried and evaporated to give 3-(1-hydroxymethyl-cyclopropyl)-3-oxo-propionitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.26 (s, 2 H) 4.03 (s, 1 H) 3.58 (br. s., 2 H) 1.15-1.16 (m, 2 H) 0.92-0.95 (m, 2 H).
Workup
- customto reach rt
- customAt this point it is quenched with 1N HCl (200 mL)
- extractionextracted with EtOAc (200 mL, ×3)
- customIt is then dried
- customevaporated
Sources & evidence
- ORD record
- ord-7cc4bd9a892a4824acd07c5c841c0174
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431584B2
Reaction notes
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