Ethyl benzoylacetate → ethyl 2-bromo-3-oxo-3-phenylpropanoate

HRID 583786ノート

反応式

HRID 583786 の反応式
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([CH:9]([Br:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 7170Ethyl benzoylacetateHCID 67184N-bromobutanimide

生成物 1

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a stirred solution of benzoylacetic acid, ethyl ester (0.01 mol) in a solvent such as, for example, chloroform is added N-bromosuccinimide (NBS, 0.01 mol), and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of benzoyl-bromoacetic acid, ethyl ester is formed, ethyl acetate is added, and the mixture is rotary evaporated to remove chloroform. To the resulting ethyl acetate mixture is added thiocarbamic acid, benzyl ester, which may be prepared as described in Step (a) above, and a suitable non-nucleophilic base such as those described in Example 17 above, and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of the desired product is formed, the reaction is washed with 0.01 M hydrochloric acid, water, brine, and dried over sodium sulfate. The mixture is rotary evaporated to give 2-benzyloxy-4-phenyl-thiazol-5-carboxylic acid, ethyl ester, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

後処理

  1. customReaction progress

出典と根拠

ORDレコード
ord-bd755813d0014a37ac1af374997a4eaf
出典データセット
uspto-grants-2005_08
特許番号
US06924276B2

反応ノート

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