Methanol → (4-(3-Fluoro-pyridin-2-yloxymethyl)-phenyl)acetohydroximoyl chloride

HRID 78150ノート

反応式

HRID 78150 の反応式
CO.[F:3][C:4]1[C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N+:20]([O-:22])=O)=[CH:14][CH:13]=2)=[N:6][CH:7]=[CH:8][CH:9]=1.C[O-].[Li+].C(Cl)[Cl:27]>[Ti](Cl)(Cl)(Cl)Cl.O>[F:3][C:4]1[C:5]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([Cl:27])=[N:20][OH:22])=[CH:14][CH:13]=2)=[N:6][CH:7]=[CH:8][CH:9]=1

参加物

7

反応物 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4177230Lithium methanolateHCID 592554403-Fluoro-2-(4-(2-nitro-ethyl)-benzyloxy)-pyridine

生成物 1

HCID 72262846(4-(3-Fluoro-pyridin-2-yloxymethyl)-phenyl)acetohydroximoyl chloride収率 88%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 962Water溶媒

実験手順

To a methanol (10 mL) solution of 3-fluoro-2-(4-(2-nitro-ethyl)-benzyloxy)-pyridine (674 mg, 2.44 mmol) described in Manufacturing Example 149-1-3 was added lithium methoxide (185 mg, 4.87 mmol), which was stirred for 5 minutes at room temperature. The reaction mixture was concentrated under a reduced pressure. To a suspension of this residue in tetrahydrofuran (10 mL) and methylene chloride (10 mL) was added titanium (IV) tetrachloride (590 μL, 5.37 mmol) under nitrogen atmosphere at −78° C., which was stirred for 1 hour at 0° C. Water was added to the reaction mixture at 0° C., which was then extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered with neutral silica gel. The filtrate was concentrated under a reduced pressure to obtain the title compound (629 mg, 88%). This compound was used in the following reaction without any further purification.

後処理

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. additionTo a suspension of this residue in tetrahydrofuran (10 mL)
  3. stirringwhich was stirred for 1 hour at 0° C
  4. extractionwhich was then extracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered with neutral silica gel
  9. concentrationThe filtrate was concentrated under a reduced pressure

出典と根拠

ORDレコード
ord-c279308ab11d4ff39f2b6ea35b72aaab
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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