2-Ethylhexanol → HCID 21934049, compound

HRID 891316Notes

Reaction equation

HRID 891316 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].[H-].[Na+].[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:24](=[O:25])[C:23](OS(C3C=CC(C)=CC=3)(=O)=O)=[C:22]([C:37]3[CH:42]=[CH:41][C:40]([S:43]([CH3:46])(=[O:45])=[O:44])=[CH:39][CH:38]=3)[CH:21]=[N:20]2)=[CH:15][CH:14]=1>C1COCC1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:24](=[O:25])[C:23]([O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH3:9])=[C:22]([C:37]3[CH:42]=[CH:41][C:40]([S:43]([CH3:46])(=[O:44])=[O:45])=[CH:39][CH:38]=3)[CH:21]=[N:20]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 77202-EthylhexanolHCID 24758Sodium hydrideHCID 219338542-(4-fluorophenyl)-4-tosyloxy-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

Product 1

HCID 21934049HCID 21934049, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethyl-1-hexanol (65 mg, 0.5 mmol) in THF (15 mL) at room temperature was added NaH (60% oil suspension) (20 mg, 0.5 mmol) and after 10 minutes 2-(4-fluorophenyl)-4-tosyloxy-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone (193 mg, 0.5 mmol) was added. The resulting mixture was stirred at room temperature for the next 2 hours. The mixture was quenched with 10% citric acid and extracted with ethyl acetate. The extract was washed with water, brine, dried with MgSO4, and purified by chromatography (silica gel, 2:1 hexanes-ethyl acetate) to provide the desired product (yield: 140 mg, 60%). mp 120-122° C. 1H NMR (300 MHz, DMSO-d6) δ 0.75 (m, 6H), 1.1 (m, 6H), 1.20 (quintet, J=7 Hz, 2H), 1.44 (m, 1H), 3.27 (s, 3H), 4.30 (d, J=6 Hz, 2H), 7.37 (t, J=9 Hz, 2H), 7.65 (m, 2H), 7.89 (d, J=9 Hz, 2H), 8.06 (d, J=9 Hz, 2H), 8.18 (s, 1H). MS (APCI+) m/z 473 (M+H)+; (APCI−) m/z 507 (M+Cl)−. Anal. calc. for C25H29FN2O4S.0.5H2O: C, 62.35; H, 6.27; N, 5.87. Found: C, 62.22; H, 6.14; N, 6.22.

Workup

  1. customThe mixture was quenched with 10% citric acid
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, brine
  4. dry with materialdried with MgSO4
  5. custompurified by chromatography (silica gel, 2:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-ff9836a0c39f4467aee46b6116f52212
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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