Oxalyl chloride → Isobutyl 4-[3-(3-ethoxy-3-oxopropyl)-4-isobutoxybenzoyl]-3-isobutoxybenzoate

HRID 2249621ノート

反応式

HRID 2249621 の反応式
[CH2:1]([O:5][C:6]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)[CH:2]([CH3:4])[CH3:3].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:32]([O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:33]([CH3:35])[CH3:34]>C(Cl)Cl.O.C(Cl)(Cl)Cl.CN(C)C=O>[CH2:48]([O:47][C:45](=[O:46])[CH2:44][CH2:43][C:38]1[CH:39]=[C:40]([CH:41]=[CH:42][C:37]=1[O:36][CH2:32][CH:33]([CH3:35])[CH3:34])[C:8]([C:7]1[CH:11]=[CH:12][C:13]([C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])=[CH:14][C:6]=1[O:5][CH2:1][CH:2]([CH3:3])[CH3:4])=[O:10])[CH3:49]

参加物

9

反応物 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178164642-Isobutoxy-4-(isobutoxycarbonyl)-benzoic acidHCID 17816468Ethyl 3-(2-isobutoxyphenyl)propanoate

生成物 1

HCID 17816553Isobutyl 4-[3-(3-ethoxy-3-oxopropyl)-4-isobutoxybenzoyl]-3-isobutoxybenzoate収率 65.2%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

In 18 ml of methylene chloride is dissolved 1.8 g of 2-isobutoxy-4-(isobutoxycarbonyl)-benzoic acid. After adding 0.7 ml of oxalyl chloride and subsequently 20 μl of N,N-dimethylformamide at ambient temperature, the mixture thus obtained is stirred at ambient temperature for one hour. Then, 1.6 g of aluminum chloride and subsequently 1.8 g of ethyl 3-(2-isobutoxyphenyl)propanoate are added at 5-10° C., and the resulting mixture is stirred at ambient temperature for one hour. The reaction mixture is added to a mixture of chloroform and water and the organic layer is separated. The organic layer thus obtained 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 2.1 g of isobutyl 4-[3-(3-ethoxy-3-oxopropyl)-4-isobutoxybenzoyl]-3-isobutoxybenzoate as a colorless oily product.

後処理

  1. customthe mixture thus obtained
  2. stirringthe resulting mixture is stirred at ambient temperature for one hour
  3. customthe organic layer is separated
  4. customThe organic layer thus obtained
  5. washis 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-d6f0e9751f6441b18d8c115e936c58ad
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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