Sodium Cyanide → 2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-hydroxyacetonitrile

HRID 1397394노트

반응식

HRID 1397394 반응식
OP([O-])(O)=O.[K+].[C-:7]#[N:8].[Na+].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][CH:19]=[C:20]([CH:22]=[O:23])[N:21]=2)=[CH:13][CH:12]=1>CN(C=O)C.O.O>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[O:18][CH:19]=[C:20]([CH:22]([OH:23])[C:7]#[N:8])[N:21]=2)=[CH:15][CH:16]=1

참가 물질

6

반응물 3

HCID 8929Sodium CyanideHCID 516951Monobasic potassium phosphateHCID 218062352-(4-Fluoro-phenyl)-oxazole-4-carbaldehyde

생성물 1

HCID 866749192-(2-(4-Fluorophenyl)oxazol-4-yl)-2-hydroxyacetonitrile수율 87.5%

시약·촉매·용매 2

HCID 962Water용매HCID 21962138N,N-Dimethylformamide--water (1/1)용매

실험 절차

KH2PO4 (712 mg, 5.23 mmol) and NaCN (251 mg, 5.12 mmol) were added to a solution of 2-(4-fluorophenyl)oxazole-4-carbaldehyde (500 mg, 2.62 mmol) in DMF-H2O (10 mL, 4:6, v/v). The resulting reaction mixture was stirred at room temperature for 1 h, then diluted with water and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-hydroxyacetonitrile (500 mg, yield 87%). 1H NMR (400 MHz, CDCl3) δ 8.07-8.02 (m, 2H), 7.88 (s, 1H), 7.20-7.16 (t, J=8.8 Hz, 2H), 5.62 (s, 1H), 4.38 (br s, 1H). MS (ESI) m/z: Calculated for C11H7FN2O2: 218.05. found: 218.8 (M+H)+.

후처리

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-689c41ec58524280b16f7bb8a9e0b01b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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