Ethyl Acetate → 4-(3-Chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazole

HRID 1295216노트

반응식

HRID 1295216 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])[CH:11]=1)[CH2:7]O)[CH3:2].S(Cl)([Cl:28])=O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:28][CH2:7][C:6]1[CH:9]=[C:10]([CH:11]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[O:12][CH2:13][C:14]1[N:15]=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:17][C:18]=1[CH3:19]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 694273333-Ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

생성물 1

HCID 229306794-(3-Chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazole수율 92%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (4.38 g) in toluene (80 ml) was added dropwise thionyl chloride (1.69 g) at room temperature. After stirring for 90 min, ethyl acetate (100 ml) was added to the reaction mixture and the mixture was washed with aqueous sodium bicarbonate and then with water. The organic layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the crystals obtained from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio) were recrystallized from ethyl acetate-hexane to give 4-(3-chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazole (4.25 g, 92%) as colorless prism crystals. melting point: 86–87° C.

후처리

  1. washthe mixture was washed with aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customthe crystals obtained from the fraction
  5. washeluted with ethyl acetate-hexane (1:4, volume ratio)
  6. customwere recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-24e6ff999b2f448fa86a8917b7447581
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241785B2

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