Methanol → (4-(Pyridin-2-yloxy)benzene)-acetohydroximoyl chloride

HRID 78252ノート

反応式

HRID 78252 の反応式
CO.[N+:3]([CH2:6][CH2:7][C:8]1[CH:20]=[CH:19][C:11]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:10][CH:9]=1)([O-])=[O:4].C[O-].[Li+].O1CCCC1.C(Cl)[Cl:30]>[Ti](Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[C:6]([Cl:30])(=[N:3][OH:4])[CH3:7].[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][C:11]1[CH:10]=[CH:9][CH:8]=[CH:20][CH:19]=1

参加物

8

反応物 5

HCID 887MethanolHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 4177230Lithium methanolateHCID 592552412-(4-(2-Nitro-ethyl)-phenoxy)-pyridine

生成物 1

HCID 86612460(4-(Pyridin-2-yloxy)benzene)-acetohydroximoyl chloride収率 98%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-76 °C

実験手順

To a methanol solution (30 mL) of 2-(4-(2-nitro-ethyl)-phenoxy)-pyridine (2.0 g, 8.2 mmol) described in Manufacturing Example 209-1-3 was added lithium methoxide (470 mg, 12 mmol), and this mixture was concentrated under a reduced pressure. Toluene was added to the residue, and the solvent was evaporated under a reduced pressure. To a solution of this residue in methylene chloride (40 mL) and tetrahydrofuran (20 mL) was added titanium (IV) tetrachloride (2.3 mL, 21 mmol) while stirring at −76° C. This suspension was stirred for 15 minutes at 0° C., and then for another 20 minutes at room temperature. The mixture was poured into ice water and stirred for 30 minutes. Ethyl acetate was added, and the organic layer was separated, washed with aqueous sodium chloride (one time), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (2.1 g, 98%).

後処理

  1. concentrationthis mixture was concentrated under a reduced pressure
  2. additionToluene was added to the residue
  3. customthe solvent was evaporated under a reduced pressure
  4. stirringThis suspension was stirred for 15 minutes at 0° C.
  5. stirringstirred for 30 minutes
  6. customthe organic layer was separated
  7. washwashed with aqueous sodium chloride (one time)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under a reduced pressure

出典と根拠

ORDレコード
ord-37c083ec716e4e90b2a664e3bd47815a
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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