Water → 2-(4-Chlorophenyl)-4-[(methoxymethoxy)methyl]-1,3-oxazole-5-carbaldehyde
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]=1참가 물질
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
- temperatureto warm to RT
- stirringstirred at RT for another 1 h
- extractionThe mixture is extracted three times with in each case 10 ml of diethyl ether
- dry with materialThe combined organic phases are dried over magnesium sulfate
- customthe solvent is removed on a rotary evaporator
- 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-e9cec58d0f0141aa83ada89ed1686513
- 출처 데이터셋
- uspto-grants-2013_05
- 특허 번호
- US08440700B2
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