tert-Butanol → N-(4-chloro-5-formylpyridin-2-yl)acetamide

HRID 870940ノート

反応式

HRID 870940 の反応式
[Cl:1][C:2]1[C:7]([CH:8]=C)=[CH:6][N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=1.N1C(C)=CC=CC=1C.CC([OH:26])(C)C.I([O-])(=O)(=O)=O.[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[C:7]([CH:8]=[O:26])=[CH:6][N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=1

参加物

8

反応物 4

HCID 6386tert-ButanolHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 86695930N-(4-chloro-5-vinylpyridin-2-yl)acetamide

生成物 1

HCID 86695931N-(4-chloro-5-formylpyridin-2-yl)acetamide収率 92.1%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of N-(4-chloro-5-vinylpyridin-2-yl)acetamide (6 g, 30.5 mmol) and 2,6-lutidine (7.11 mL, 61.0 mmol) in a mixture of dioxane (110 mL) and water (25 mL) at 0° C. was added osmium tetroxide, 2.5 wt % solution in 2-methyl-2-propanol (9.58 mL, 30.5 mmol) followed by the addition of sodium periodate (19.58 g, 92 mmol) and the reaction was stirred for 4 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine solution, dried over sodium sulphate, concentrated under reduced pressure. The residue was purified by silica column using hexane/Ethyl acetate to yield N-(4-chloro-5-formylpyridin-2-yl)acetamide as an off-white solid (5.8 g, 28.1 mmol, 92% yield). LCMS (ESI) m/e 197.0 [(M)−, calcd for C8H6ClN2O2197.04] LC/MS retention time (method A): tR=1.21 min; 1H NMR (400 MHz, DMSO-d6) δ 11.20 (s, 1H), 10.18 (s, 1H), 8.76 (s, 1H), 8.27 (s, 1H), 2.16 (s, 3H).

後処理

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organic layers were washed with brine solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica column

出典と根拠

ORDレコード
ord-e9541f4d1d26493a87472a07c1b73b1b
出典データセット
uspto-grants-2015_03
特許番号
US08969564B2

反応ノート

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