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2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide → Rac-7-{[2-(tert-butyl-dimethyl-silanyl)-1-dimethylsulfamoyl-1h-imidazol-4-yl]-hydroxy-methyl}-5-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 1694794
ノート
印刷プレビュー

反応式

HRID 1694794 の反応式
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].[CH2:19]([O:21][C:22]([C:24]1[O:25][C:26]2[C:32]([CH:33]=[O:34])=[CH:31][C:30]([CH3:35])=[CH:29][C:27]=2[CH:28]=1)=[O:23])[CH3:20]>C1COCC1.CCCCCCC>[CH2:19]([O:21][C:22]([C:24]1[O:25][C:26]2[C:32]([CH:33]([C:9]3[N:8]=[C:7]([Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])[N:6]([S:3](=[O:4])(=[O:5])[N:2]([CH3:18])[CH3:1])[CH:10]=3)[OH:34])=[CH:31][C:30]([CH3:35])=[CH:29][C:27]=2[CH:28]=1)=[O:23])[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 589519217-Formyl-5-methyl-benzofuran-2-carboxylic acid ethyl ester

生成物 1

HCID 58951952Rac-7-{[2-(tert-butyl-dimethyl-silanyl)-1-dimethylsulfamoyl-1h-imidazol-4-yl]-hydroxy-methyl}-5-methyl-benzofuran-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 8900
Heptane
溶媒

実験手順

A solution of 2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (1.0 g) in THF (10 ml) was cooled under an Argon atmosphere to −78° C. n-Buthyllithium solution (1.6 M in heptane, 2.37 ml) were added dropwise. After stirring for 1 hr at −78° C. a solution of 7-formyl-5-methyl-benzofuran-2-carboxylic acid ethyl ester (963 mg) in THF (10 ml) was added dropwise. Stirring was continued for 15 min at −78° C., then the reaction mixture was warmed up to r.t. overnight. After quenching with water, the mixture was extracted with EtOAc. The organics were dried over MgSO4, filtrated and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1) to give rac-7-{[2-(tert-butyl-dimethyl-silanyl)-1-dimethylsulfamoyl-1H-imidazol-4-yl]-hydroxy-methyl}-5-methyl-benzofuran-2-carboxylic acid ethyl ester as light yellow amorphous solid; MS (ISP): 522.3 ((M+H)+.).

後処理

  1. additionwere added dropwise
  2. additionwas added dropwise
  3. customAfter quenching with water
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane→cyclohexane/EtOAc 1:1)

出典と根拠

ORDレコード
ord-928f8e0546c844bd81bca93d307fdc4f
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158668B2

反応ノート

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