Tetrahydrofuran → 1-(6-Chloropyridazin-3-yl)ethan-1-one

HRID 2038760노트

반응식

HRID 2038760 반응식
[Cl:1][C:2]1[N:7]=[N:6]C(C#N)=CC=1.[CH3:10][Mg]Br.[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[Cl:1][C:2]1[N:7]=[N:6][C:13]([C:17](=[O:16])[CH3:10])=[CH:14][CH:15]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 133828716-Chloropyridazine-3-carbonitrileHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 468356481-(6-Chloropyridazin-3-yl)ethan-1-one

실험 절차

A solution of 6-chloro-pyridazine-3-carbonitrile (prepared according to MacDonald et al., WO/2008/068277) (100 mg, 0.71 mmol) in dry THF (3.6 mL) was cooled to −50° C. in a dry ice/acetone bath. Methylmagnesium bromide (1.0 M in MePh/THF, 0.54 mL, 0.75 mmol) was added via syringe in one portion. The cold bath was removed and the reaction was stirred for 1.5 h. To the reaction mixture was added saturated aqueous NH4Cl and this mixture was extracted with EtOAc (3×). The combined organics were dried over MgSO4 and concentrated. The resulting residue was purified by flash chromatography (silica, 0→4% MeOH/CH2Cl2) to give 34 mg of 1-(6-chloro-pyridazin-3-yl)-ethanone as a brown semi-solid, m/z 157.3 [M+H]+.

후처리

  1. customThe cold bath was removed
  2. additionTo the reaction mixture was added saturated aqueous NH4Cl
  3. extractionthis mixture was extracted with EtOAc (3×)
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (silica, 0→4% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-c522e294b1c944cfb89f43ad5a88cddb
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575360B2

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