2,2-Dimethylbutanol → 6-Phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether

HRID 1084771ノート

反応式

HRID 1084771 の反応式
[OH-].[Na+].[CH3:3][C:4]([CH3:9])([CH2:7][CH3:8])[CH2:5][OH:6].Cl[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:3][C:4]([CH3:9])([CH2:7][CH3:8])[CH2:5][O:6][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=1

参加物

6

反応物 3

HCID 144542,2-DimethylbutanolHCID 14798Sodium HydroxideHCID 138492412-Chloromethyl-6-phenoxypyridine

生成物 1

HCID 148789686-Phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether収率 23%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒2 回

実験手順

4.4 Grams of a 45% aqueous sodium hydroxide solution, 100 mg of tetrabutylammonium bromide and 5 ml of toluene were mixed, and to the resulting mixture, a solution of 0.7 g of 2,2-dimethylbutanol and 1.72 g of 2-chloromethyl-6-phenoxypyridine in 10 ml of toluene was added at room temperature under a nitrogen atmosphere. After 12 hours, the reaction solution was poured into hydrochloric acid-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was treated by preparative thin layer chromatography (developing solvent, hexane: ethyl acetate=5:1) to obtain 0.45 g of desired 6-phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether [present compound (17)] as an oily product.

後処理

  1. extractionextracted twice with diethyl ether
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue was treated by preparative thin layer chromatography (developing solvent, hexane: ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-d68c367c4f9445ab89a4d1a84350d82c
出典データセット
uspto-grants-1991_04
特許番号
US05006538

反応ノート

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