Benzyl Chloride → 6-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

HRID 556342

反応式

HRID 556342 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O.CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][C:9]=2[O:8][N:7]=1)=[O:5])[CH3:2]

参加物

7

反応物 3

HCID 7503Benzyl ChlorideHCID 10796Cesium carbonateHCID 136216618Ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate

生成物 1

HCID 669926006-Benzyloxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
56 °C

実験手順

To a solution of 0.98 g (4.73 mMol) 6-hydroxy-benzo[d]isoxazole-3-carboxylic acid ethyl ester [preparation see: J. Am. Chem. Soc. 97 (1974), 7305] in 100 ml acetone, 545 μl (4.73 mMol) benzylchloride, 3.08 g (9.46 mMol) Cs2CO3 und 10 mg NaI are added. Then the mixture is stirred for 2 h at rt and 5 h at 56° C. The reaction mixture is diluted with EtOAc and water, the aq. phase separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated after addition of 10 g SiO2. The resulting powder is put on top of a chromatography column (SiO2) and the title compound eluated with hexan/EtOAc 9:1→8:2→7:3: MS: [M+1]+=298; TLC(hexane/EtOAc 3:1): Rf=0.54.

後処理

  1. customthe aq. phase separated off
  2. extractionextracted with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. additionafter addition of 10 g SiO2

出典と根拠

ORDレコード
ord-d50dad6058f1460a8e5533089bfa5bdd
出典データセット
uspto-grants-2011_11
特許番号
US08058276B2

関連ノート

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