Dimethylformamide → 5-[2-[4-(5-Methyl-2-phenyl-4-oxazolyl)methoxyphenyl]ethyl]-4-methoxymethoxymethyl-2-phenyloxazole

HRID 1295263

반응식

HRID 1295263 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:12][C:11]=2[CH2:21][O:22][CH2:23][O:24][CH3:25])=[CH:4][CH:3]=1.Cl[CH2:27][C:28]1[N:29]=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:31][C:32]=1[CH3:33].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:33][C:32]1[O:31][C:30]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[N:29][C:28]=1[CH2:27][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:12][C:11]=2[CH2:21][O:22][CH2:23][O:24][CH3:25])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 229307245-[2-(4-Hydroxyphenyl)ethyl]-4-methoxymethoxymethyl-2-phenyl-1,3-oxazole

생성물 1

HCID 99361405-[2-[4-(5-Methyl-2-phenyl-4-oxazolyl)methoxyphenyl]ethyl]-4-methoxymethoxymethyl-2-phenyloxazole수율 100.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A mixture of 5-[2-(4-hydroxyphenyl)ethyl]-4-methoxymethoxymethyl-2-phenyloxazole (3.12 g), 4-chloromethyl-5-methyl-2-phenyloxazole (2.28 g), potassium carbonate (1.27 g) and N,N-dimethylformamide (50 ml) was stirred at 90° C. for 15 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography, and 5-[2-[4-(5-methyl-2-phenyl-4-oxazolyl)methoxyphenyl]ethyl]-4-methoxymethoxymethyl-2-phenyloxazole (4.70 g, yield 85%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 124–125° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with dilute hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8f3eb6e5c043409dabcdc8e97847c7ff
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241785B2

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