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

HRID 508167노트

반응식

HRID 508167 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-78cefb94109c42eda58c055375f8561c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09095582B2

반응 노트

불러오는 중…