Sodium Carbonate → Ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-hydroxycyclopentan-1-yl}methyl]phenoxy]acetate

HRID 377328ノート

反応式

HRID 377328 の反応式
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH2:22][CH2:21][CH2:20][C:19]=3[CH2:23][C:24]3[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=3)[O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2N=C(C3C(CC4C=C(C=CC=4)OCC(OCC)=O)CCC=3)[O:46]C=2C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH2:22][CH2:21][CH2:20][C:19]3([CH2:23][C:24]3[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=3)[O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[OH:46])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 54031249Ethyl [3-[[2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl]methyl]phenoxy]acetateHCID 54507446Ethyl [3-[[2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]methyl]phenoxy]acetate

生成物 1

HCID 86755137Ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-hydroxycyclopentan-1-yl}methyl]phenoxy]acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of a mixture (300 mg) of ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl}methyl]phenoxy]acetate and ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl}methyl]phenoxy]acetate in methylene chloride (10 ml) were added sodium carbonate (100 mg) and m-chloroperbenzoic acid (200 mg) at 0° C. After being stirred for 2 hours, the reaction mixture was washed with water and brine and dried over magnesium sulfate. After the solvent was evaporated, the residue containing a mixture of ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1,2-epoxycyclopentan-1-yl}methyl]phenoxy]acetate and ethyl [3-[(2-(4,5-diphenyloxazol-2-yl)-2,3-epoxycyclopentan-1-yl]methyl]phenoxy]acetate was dissolved in a mixture of ethyl acetate-ethanol (20 ml-10 ml), and thereto was added 10% palladium on carbon (50 mg). After being stirred for 6 hours under hydrogen atmosphere, the reaction mixture was filtered. The solvent was evaporated in vacuo, the residue was chromatographed on silica gel. The first fraction gave ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-hydroxycyclopentan-1-yl}methyl]phenoxy]acetate (70 mg).

後処理

  1. washthe reaction mixture was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customAfter the solvent was evaporated
  4. additionthe residue containing
  5. additiona mixture of ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1,2-epoxycyclopentan-1-yl}methyl]phenoxy]acetate and ethyl [3-[(2-(4,5-diphenyloxazol-2-yl)-2,3-epoxycyclopentan-1-yl]methyl]phenoxy]acetate
  6. dissolutionwas dissolved in a mixture of ethyl acetate-ethanol (20 ml-10 ml)
  7. additionwas added 10% palladium on carbon (50 mg)
  8. stirringAfter being stirred for 6 hours under hydrogen atmosphere
  9. filtrationthe reaction mixture was filtered
  10. customThe solvent was evaporated in vacuo
  11. customthe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-1187e59d948747b992bd2d38962a57fc
出典データセット
uspto-grants-2000_02
特許番号
US06025375

反応ノート

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