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

HRID 450310노트

반응식

HRID 450310 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dc4cce6555d94113932a92ff1a045532
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486954B2

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