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

HRID 45161Notes

Reaction equation

HRID 45161 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-26bcfde5db4c4e989cb7919fffe1ef09
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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