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

HRID 1715401
ノート
印刷プレビュー

反応式

HRID 1715401 の反応式
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]
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 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0c76a6629034409b9050829f3d487c35
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07799805B2

反応ノート

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