Water → HCID 58423229, 화합물

HRID 1398026노트

반응식

HRID 1398026 반응식
[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].FC(F)(F)S(O[CH2:19][C:20]([F:23])([F:22])[F:21])(=O)=O.O>CN(C=O)C.[Cl-].[Na+].O>[F:1][C:2]1[C:9]([O:10][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 196072232-Fluoro-3-hydroxybenzonitrile

생성물 1

HCID 58423229HCID 58423229, 화합물수율 81.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A stirred solution of 2-fluoro-3-hydroxybenzonitrile (800 mg, 5.83 mmol) in DMF (10 mL) at 0° C. was treated portionwise with NaH (280 mg, 7.00 mmol) (60% oil dispersion). The reaction mixture was then stirred for 0.5 h and 2,2,2-trifluoroethyl trifluoromethanesulfonate (1490 mg, 6.42 mmol) was added. The reaction was allowed to warm to rt overnight with stirring. The reaction mixture was then treated with water (40 mL) and brine (5 mL) and extracted with ethyl acetate (˜50 mL). The organic extract was washed with water, dried over anhydrous Na2SO4, filtered and conc. in vacuo to afford a residue which was purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes) to yield the title compound as a white solid (1040 mg, 81%). 1H NMR (400 MHz, MeOD) δ ppm 7.56 (td, 1 H), 7.47-7.38 (m, 1 H), 7.38-7.24 (m, 1 H), 4.73 (q, 2 H); m/z 220.

후처리

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate (˜50 mL)
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered and conc. in vacuo
  7. customto afford a residue which
  8. customwas purified via silica gel chromatography (10% to 30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-fee0d2cb4fc144ec9df6cb80da812aba
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901307B2

반응 노트

불러오는 중…