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

HRID 2249629노트

반응식

HRID 2249629 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-28672dedda664cd0891949bc994cca2a
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314888B1

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