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

HRID 1295216ノート

反応式

HRID 1295216 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24e6ff999b2f448fa86a8917b7447581
出典データセット
uspto-grants-2007_07
特許番号
US07241785B2

反応ノート

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