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Ethyl Acetate → N-(4-Chloro-3-hydroxymethyl-benzyl)-3,3,3-trifluoro-propionamide

HRID 1715401
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HRID 1715401 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([SiH2][O:24][C:25](C)(C)[C:26]1[CH:27]=[C:28]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH2:29][NH:30][C:31](=[O:37])[CH2:32][C:33]([F:36])([F:35])[F:34])(C)(C)C.CCOC(C)=O>C1COCC1>[Cl:41][C:40]1[CH:39]=[CH:38][C:28]([CH2:29][NH:30][C:31](=[O:37])[CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:27][C:26]=1[CH2:25][OH:24]
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 137329921N-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-3,3,3-trifluoro-propionamide

생성물 1

HCID 67148258N-(4-Chloro-3-hydroxymethyl-benzyl)-3,3,3-trifluoro-propionamide수율 65.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

TBAF (1M in THF, 9.10 mL, 9.10 mmol) was added to a sol. of N-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-3,3,3-trifluoro-propionamide (1.80 g, 4.55 mmol) in THF (45 mL) at 0° C. The mixture was stirred for 1 h while warming up to rt. EtOAc (100 mL) was added, and the mixture was washed with aq. sat. NH4Cl (3×) and water (4×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 70:30) yielded the title compound (835 mg, 65%). LC-MS: tR=0.76 min; ES+: 323.02.

후처리

  1. washthe mixture was washed with aq. sat. NH4Cl (3×) and water (4×)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (EtOAc/heptane 70:30)

출처 및 근거

ORD 기록
ord-0c76a6629034409b9050829f3d487c35
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07799805B2

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