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

HRID 19796노트

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HRID 19796 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a17b959c3109486ba4c2f84f8763b206
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745477B2

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