Carbonyl bromide → 2-(4-Methylsulphinylphenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine

HRID 586614

反応式

HRID 586614 の反応式
[CH2:1]([C:8]1[CH2:12][CH2:11][CH2:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13][S:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20](=O)[CH2:21]Br)=[CH:18][CH:17]=1)=[O:15].C([O-])(O)=O.[Na+].BrC(Br)=O>CO.C(Cl)Cl.O.CCCCCC.CCOCC>[CH3:13][S:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]2[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:8]3[N:9]([CH:21]=2)[CH2:10][CH2:11][CH2:12]3)=[CH:18][CH:17]=1)=[O:15]

参加物

9

反応物 4

HCID 79057Carbonyl bromideHCID 2240185-benzyl-3,4-dihydro-2H-pyrroleHCID 516892Sodium BicarbonateHCID 12795537HCID 12795537、化合物

生成物 1

HCID 99669092-(4-Methylsulphinylphenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizine収率 12%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 21584099Diethylether hexane溶媒

実験手順

2-Benzyl-1-pyrroline (2.0 g, 80% strength, 10 mmol), dissolved in MeOH (30 ml), is treated with a solution of 4-methylsulphinylphenacyl bromide (2.1 g, 8 mmol) in CH2Cl2 (10 ml) and then with NaHCO3 (1.5 g, 18 mmol) and the mixture is stirred at RT until a TLC sample (Al2O3, hexane/ether 9:1) indicates the complete reaction of the bromoketone (Rf 0.75) and an adequate formation of product (Rf=0.2) (48 h). After addition of water (50 ml), the mixture is extracted with diethyl ether (3×30 ml), and the combined extracts are dried over Na2SO4 sicc. and concentrated. The residue is purified by CC (Al2O3, hexane/ether 1:1). 0.3 g (12%) of the compound sought is isolated.

後処理

  1. customan adequate formation of product (Rf=0.2) (48 h)
  2. extractionthe mixture is extracted with diethyl ether (3×30 ml)
  3. dry with materialthe combined extracts are dried over Na2SO4 sicc
  4. concentrationand concentrated
  5. customThe residue is purified by CC (Al2O3, hexane/ether 1:1)

出典と根拠

ORDレコード
ord-3c0a79815a8b4c219fdaf96779b8c705
出典データセット
uspto-grants-2005_08
特許番号
US06936632B2

関連ノート

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