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

HRID 913001ノート

反応式

HRID 913001 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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) δ (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%).

後処理

  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

出典と根拠

ORDレコード
ord-888f2b8436ea4022866f489cd13cff63
出典データセット
uspto-grants-2011_09
特許番号
US08026261B2

反応ノート

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