Tetrabutylammonium Fluoride → (4-Tert-butyl-benzyl)-[2-(3-ethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 19796ノート

反応式

HRID 19796 の反応式
[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[C:17][Si](C)(C)C)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[CH:17])[CH:11]=1)([CH3:3])([CH3:4])[CH3:2]

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 68560300(4-Tert-butyl-benzyl)-[2-(3-trimethylsilanylethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

生成物 1

HCID 86613993(4-Tert-butyl-benzyl)-[2-(3-ethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester収率 84.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

To a solution of (4-tert-butyl-benzyl)-[2-(3-trimethylsilanylethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (440 mg, 0.949 mmol) in THF (7.6 ml) was added a 1 molar solution of TBAF in THF (949 μl, 0.949 mmol) at −78° C. After 15 min at −78° C. the solution was allowed to warm to 0° C. for 30 min. Then brine was added and the mixture was extracted with ether. The combined ether layers were dried (Na2SO4) and evaporated and the remaining residue was purified by chromatography (pentane/ether 100:0 to 90:10) to obtain the title compound as a colorless oil (314 mg, 84%). MS (ISP) 392.3 (M+H)+.

後処理

  1. extractionthe mixture was extracted with ether
  2. dry with materialThe combined ether layers were dried (Na2SO4)
  3. customevaporated
  4. customthe remaining residue was purified by chromatography (pentane/ether 100:0 to 90:10)

出典と根拠

ORDレコード
ord-a17b959c3109486ba4c2f84f8763b206
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

反応ノート

読み込み中…