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

HRID 450310ノート

反応式

HRID 450310 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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, 2H) 4.03 (s, 1H) 3.58 (br. s., 2H) 1.15-1.16 (m, 2H) 0.92-0.95 (m, 2H).

後処理

  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

出典と根拠

ORDレコード
ord-dc4cce6555d94113932a92ff1a045532
出典データセット
uspto-grants-2013_07
特許番号
US08486954B2

反応ノート

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