Triethylamine → Benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester

HRID 426227ノート

反応式

HRID 426227 の反応式
Cl[C:2]1[C:3]([F:20])=[N:4][C:5]([F:19])=[C:6]([F:18])[C:7]=1[CH2:8][O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>[Pd].C(O)C>[F:19][C:5]1[C:6]([F:18])=[C:7]([CH2:8][O:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[C:3]([F:20])[N:4]=1

参加物

5

反応物 2

HCID 8471TriethylamineHCID 59184703Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester

生成物 1

HCID 59184767Benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester収率 85.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester (4.52 g, 15 mmol), anhydrous ethanol (50 ml), 10% palladium on carbon (500 mg), and triethylamine (2.5 ml, 18 mmol) were placed into a 500 ml bottle. The mixture was hydrogenated under hydrogen atmosphere (50 psi) for 1.5 hr. The reaction mixture was filtered through celite pad and the pad was washed with ethanol. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:15)) to afford 3.43 g (85%) of benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester as a white solid. m.p. 73-76° C.; 1H NMR (200 MHz, CDCl3) δ 5.52 (2H, s), 6.95 (1H, m), 7.30-7.70 (3H, m), 8.09-8.15 (2H, m).

後処理

  1. customfor 1.5 hr
  2. filtrationThe reaction mixture was filtered through celite pad
  3. washthe pad was washed with ethanol
  4. customThe combined filtrate was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:15))

出典と根拠

ORDレコード
ord-3c8e0d5ac3ed4e4d94001b05d4a9f075
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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