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

HRID 1751824Notes

Reaction equation

HRID 1751824 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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, 21-1), 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.

Workup

  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)

Sources & evidence

ORD record
ord-1f11cedae2df4ebb8efd5562fe1ec751
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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