Water → 2-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carbaldehyde

HRID 508167ノート

反応式

HRID 508167 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][CH2:15][O:16][CH3:17])[N:12]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:25]=[O:26].O>C(OCC)C.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH:25]=[O:26])=[C:11]([CH2:13][O:14][CH2:15][O:16][CH3:17])[N:12]=2)=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 582842652-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazoleHCID 178418339Butyllithium

生成物 1

HCID 582843772-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carbaldehyde

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

200 mg (0.91 mmol) of the crude product from Example 40A are initially charged in 3.5 ml of dry diethyl ether and cooled to −78° C. 0.63 ml (1.00 mmol) of a 1.6 M solution of n-butyllithium in hexane are slowly added dropwise. The reaction mixture is stirred at −78° C. for 1 h. 0.21 ml (2.74 mmol) of N,N-dimethylformamide is then slowly added dropwise. The mixture is allowed to warm to RT and stirred at RT for another 1 h. The mixture is then poured into about 3 ml of water. The mixture is extracted three times with in each case 10 ml of diethyl ether. The combined organic phases are dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 20:1→2:1).

後処理

  1. temperatureto warm to RT
  2. stirringstirred at RT for another 1 h
  3. extractionThe mixture is extracted three times with in each case 10 ml of diethyl ether
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. customthe solvent is removed on a rotary evaporator
  6. customThe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 20:1→2:1)

出典と根拠

ORDレコード
ord-78cefb94109c42eda58c055375f8561c
出典データセット
uspto-grants-2015_08
特許番号
US09095582B2

反応ノート

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