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

HRID 1691358노트

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HRID 1691358 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 8857Ethyl Acetate용매

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온도
-76 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-db329711aaac492894c9ea30b57e6ca4
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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