Phenylacetyl chloride → 2,2,2-trichloro-1-[4-(2-phenylacetyl)-1H-pyrrol-2-yl]-1-ethanone

HRID 47257

反応式

HRID 47257 の反応式
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]([Cl:21])([Cl:20])[C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)=[O:14].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Cl:21][C:12]([Cl:11])([Cl:20])[C:13]([C:15]1[NH:16][CH:17]=[C:18]([C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:19]=1)=[O:14]

参加物

5

反応物 3

HCID 7679Phenylacetyl chlorideHCID 3214872-(Trichloroacetyl)pyrroleHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 27636082,2,2-trichloro-1-[4-(2-phenylacetyl)-1H-pyrrol-2-yl]-1-ethanone収率 60%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a dry flask, phenylacetyl chloride (1 equivalent) was combined with 2-trichloroacetyl pyrrole (1 equivalent) in a minimum amount of dichloromethane (DCM). To the resulting solution, at ambient temperature, was added aluminum trichloride (1 equivalent). After 2 hours, the reaction mixture was applied directly onto a silica gel column. Gradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 1 in 60% yield. 1H NMR (CDCl3) δ4.0 (s, 2H), 7.1-7.35 (m, 7H), 9.7 (br s, NH). HPLC using method B (as described below for Example 5) provided retention time of 4.9 minutes. LC/MS (M+1) 330.2, (M−1) 328.1.

後処理

  1. washGradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 1 in 60% yield
  2. customprovided retention time of 4.9 minutes

出典と根拠

ORDレコード
ord-ca59458ffa184794b3938b60ede37483
出典データセット
uspto-grants-2004_03
特許番号
US06699865B2

関連ノート

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