Oxalyl chloride → Ethyl 3-[5-(3,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoate

HRID 2249629ノート

反応式

HRID 2249629 の反応式
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH:14]=1)[C:9]([OH:11])=O)[CH:2]([CH3:4])[CH3:3].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:30]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:31]([CH3:33])[CH3:32]>C(Cl)Cl.C(Cl)(Cl)Cl.CN(C)C=O>[CH2:16]([O:15][C:13]1[CH:12]=[C:8]([CH:7]=[C:6]([O:5][CH2:1][CH:2]([CH3:3])[CH3:4])[CH:14]=1)[C:9]([C:38]1[CH:39]=[CH:40][C:35]([O:34][CH2:30][CH:31]([CH3:32])[CH3:33])=[C:36]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:37]=1)=[O:11])[CH:17]([CH3:19])[CH3:18]

参加物

8

反応物 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 17816468Ethyl 3-(2-isobutoxyphenyl)propanoateHCID 178165213,5-Diisobutoxybenzoic acid

生成物 1

HCID 17816456Ethyl 3-[5-(3,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoate収率 84.2%

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

In 11 ml of methylene chloride is dissolved 1.11 g of 3,5-diisobutoxybenzoic acid. To the solution thus obtained, 0.44 ml of oxalyl chloride is added at ambient temperature, and then 20 μl of N,N-dimethylformamide is added and stirred at ambient temperature for 2 hours. Then, at −20° C., 1.67 g of aluminum chloride is added and thereafter 1.15 g of ethyl 3-(2-isobutoxyphenyl)propanoate is added, and the mixture thus obtained is stirred at 5-10° C. for 10 minutes. The reaction mixture is added to a mixture of chloroform and ice water, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1) to obtain 1.75 g of ethyl 3-[5-(3,5-diisobutoxybenzoyl)-2-isobutoxyphenyl]propanoate as a yellow-colored oily product.

後処理

  1. customTo the solution thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred at 5-10° C. for 10 minutes
  4. customthe organic layer is separated
  5. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-28672dedda664cd0891949bc994cca2a
出典データセット
uspto-grants-2008_01
特許番号
US07314888B1

反応ノート

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