Triethylamine → 6-[3-(Tert-butyl-dimethyl-silanyloxy)-propoxy]-nicotinonitrile

HRID 734435ノート

反応式

HRID 734435 の反応式
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.CCN(CC)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C.[Cl-].[Na+].O>[C:4]([Si:1]([CH3:3])([CH3:2])[O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1)([CH3:7])([CH3:6])[CH3:5]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 431521396-(3-Hydroxypropoxy)nicotinonitrile

生成物 1

HCID 578454316-[3-(Tert-butyl-dimethyl-silanyloxy)-propoxy]-nicotinonitrile収率 69.5%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of t-butyldimethylsilyl chloride (0.93 g, 6.17 mmol) in CH2Cl2 (25 mL) was added 6-(3-hydroxypropoxy)nicotinonitrile (Example 66, 1 g, 5.61 mmol), Et3N (0.62 g, 6.17 mmol), and DMAP (0.014 g, 0.11 mmol). The mixture was stirred at rt for 18 h. The reaction mixture was diluted with brine and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography (2:1 hexanes/EtOAc) to give the title compound (1.14 g, 69%). 1H NMR (400 MHz, CDCl3) δ 8.40 (dd, 1H), 7.69 (dd, 1H), 6.72 (dd, 1H), 4.40 (t, 2H), 3.73 (t, 2H), 1.90-1.98 (m, 2H), 0.82 (s, 9H), 0.02 (s, 6H).

後処理

  1. extractionextracted with CH2Cl2 (3×25 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by silica gel flash chromatography (2:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-c52599b7f28e4e838799b88875c3af98
出典データセット
uspto-grants-2009_09
特許番号
US07592361B2

反応ノート

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