Water → 6-Methoxy-2-(Phenylmethylthio)-3-Pyridinecarboxylic Acid, Methyl Ester

HRID 248297노트

반응식

HRID 248297 반응식
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:12]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[C:14]([O:22][CH3:23])[N:13]=1.O>CN(C)C=O>[CH3:23][O:22][C:14]1[N:13]=[C:12]([S:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 10821376Methyl 2-fluoro-6-methoxynicotinate

생성물 1

HCID 143719726-Methoxy-2-(Phenylmethylthio)-3-Pyridinecarboxylic Acid, Methyl Ester수율 70.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of 0.8 g (0.0161 mol) of 50% sodium hydride (in mineral oil), which had been washed with hexanes, in 20 mL dry dimethylformamide cooled to -5° under nitrogen was added dropwise 1.9 mL (0.0161 mol) benzyl mercaptan. The suspension was stirred at room temperature for 1 hour, cooled to 0°, and a solution of 3.2 g (0.0147 mol) of the product of Example 13 in 20 mL dry dimethylformamide was added dropwise. After warming to room temperature, the solution was poured into water and extracted with ether. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, and evaporated to an oil which was purified by flash chromatography to afford 3.0 g (64%) of a yellow solid: m.p. 67°-71°; NMR (CDCl3, 200 Mhz) 3.88 (3H, s), 3.96 (3H, s), 4.46 (2H, s), 6.44 (1H, d, J=9Hz), 7.2°-7.5 (5H, m), 8.1 (1H, d, J=9 Hz); IR (nujol) 1700, 1580, 1305, 1255 cm-1.

후처리

  1. washhad been washed with hexanes, in 20 mL dry dimethylformamide
  2. temperaturecooled to -5° under nitrogen
  3. temperaturecooled to 0°
  4. temperatureAfter warming to room temperature
  5. extractionextracted with ether
  6. washThe combined organic layers were washed with water and with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to an oil which
  9. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-5e59bc6d21334ac7baa7bc7d1e5d404b
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05209770

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