Ammonium Hydroxide → 5-Benzyloxy-2-difluoromethyl-1H-pyridin-4-one

HRID 1187467노트

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HRID 1187467 반응식
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([CH:15]([F:17])[F:16])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+:20].C(Cl)Cl.CCOC(C)=O>C(O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([CH:15]([F:17])[F:16])[NH:20][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 21226138Dichloromethane ethylacetateHCID 598182925-Benzyloxy-2-difluoromethyl-pyran-4-one

생성물 1

HCID 672821655-Benzyloxy-2-difluoromethyl-1H-pyridin-4-one수율 74%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

5-Benzyloxy-2-difluoromethyl-pyran-4-one (0.47 g, 1.9 mmol) was dissolved in ethanol (15 mL) to give a slightly yellow clear solution. Ammonium hydroxide (28-30% aqueous solution, 15 mL, 235 mmol) was added at room temperature. The resulting solution was stirred at ambient temperature for 24 hours. The progress of the reaction was monitored by TLC (CH2Cl2/EtOAc, 7/3, v/v) and HPLC Method 2. Volatiles were removed in vacuo and the residue was purified by column chromatography on silica (95/5 then 85/15 CH2Cl2/MeOH, v/v) to give the title compound as a light yellow solid (0.35 g, 74%) with a HPLC purity (peak percent area) of 98.2%. 1H NMR (300 MHz, DMSO-D6) (ppm): 10.99 (br. s, 1H), 8.22 (s, 1H), 7.32-7.32 (m, 5H), 7.06 (s, 1H), 6.75 (t, J=55.4 Hz, 1H), 5.23 (s, 2H); MS (m/z) 252 [M+1]+, 192.2, 91.3 (100%).

후처리

  1. customto give a slightly yellow clear solution
  2. customVolatiles were removed in vacuo
  3. customthe residue was purified by column chromatography on silica (95/5

출처 및 근거

ORD 기록
ord-d7cab18beb574ad9958f98478ef2ef47
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673943B2

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