Dichloromethane → (+/-)-2-tert-butyl 4-chloro 5-(4-(1-tosyloxy-but-2-oxy) benzyl)oxy 3(2H)-pyridazinone

HRID 1516047ノート

反応式

HRID 1516047 の反応式
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH2:25][CH3:26])[CH2:23][OH:24])=[CH:17][CH:16]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].ClCCl.[C:30]1(C)[C:31]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1.[CH:41](N(C(C)C)CC)(C)C>O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH:22]([CH2:25][CH3:26])[CH2:23][O:24][S:36]([C:31]3[CH:30]=[CH:35][C:34]([CH3:41])=[CH:33][CH:32]=3)(=[O:37])=[O:38])=[CH:19][CH:20]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8623o-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59678644(+/-)-2-tert-butyl-4-chloro-5-(4-(1-hydroxy-but-2-oxy)benzyl)oxy-3(2H)-pyridazinone

生成物 1

HCID 59678622(+/-)-2-tert-butyl 4-chloro 5-(4-(1-tosyloxy-but-2-oxy) benzyl)oxy 3(2H)-pyridazinone収率 77.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Into a 10 mL round bottom flask was added the product of Example 3E (0.05 g, 0.13 mmol) followed by dichloromethane (2 mL). Toluenesulfonyl chloride (0.075 g, 0.39 mmol), 4-N,N-dimethylaminopyridine (0.048 g, 0.39 mmol) and diisopropylethylamine (0.05 g, 0.39 mmol, 68.7 μl) were then added in succession to the reaction mixture and this was stirred for 35 minutes. Water was then added to the mixture and the solution poured into a separatory funnel and the layers separated. The organic layer was washed with water and brine and dried over magnesium sulfate. The crude oil obtained after filtration and concentration was purified by silica gel flash chromatography (hexanes:ethyl acetate) to obtain 54 mg (77%) of the desired compound as a thick colorless oil. 1H (CDCl3) δ (ppm): 7.74 (3H, two singlets), 7.3 (m, 4H), 6.8 (d, 2H), 5.2 (s, 2H), 4.38 (p, 1H), 4.15 (m, 2H), 2.44 (s, 3H), 1.72 (m, 2H), 1.6 (s, 9H), 0.95 (t, 3H); 13C (CDCl3) δ (ppm): 159.2, 158.5, 153.9, 145.1, 133, 130, 129, 128.1, 127.2, 125.4, 118.5, 116.5, 71.9, 70.2, 66.6, 28.1, 24.2, 21.8, 9.4.

後処理

  1. additionthe solution poured into a separatory funnel
  2. customthe layers separated
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe crude oil obtained
  6. filtrationafter filtration and concentration
  7. customwas purified by silica gel flash chromatography (hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-b9a2f5a4555b45dfa8f77b59388bee06
出典データセット
uspto-grants-2012_07
特許番号
US08226929B2

反応ノート

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