Acetonitrile → 3-(1-Hydroxymethyl-cyclopropyl)-3-oxo-propionitrile

HRID 1971427Notes

Reaction equation

HRID 1971427 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]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2724682Lithium diisopropylamideHCID 22934721Methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Product 1

HCID 593940603-(1-Hydroxymethyl-cyclopropyl)-3-oxo-propionitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customto reach rt
  2. customAt this point it is quenched with 1N HCl (200 mL)
  3. extractionextracted with EtOAc (200 mL, ×3)
  4. customIt is then dried
  5. customevaporated

Sources & evidence

ORD record
ord-7cc4bd9a892a4824acd07c5c841c0174
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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