Benzyl Alcohol → HCID 68284297, compound

HRID 571617Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:34])[N:14]([CH3:33])[N:15]=[C:16]([CH2:28][O:29][CH2:30][O:31][CH3:32])[C:17]=1S(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[H-].[Na+]>CN(C=O)C.O>[CH2:10]([C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:12]1[C:13](=[O:34])[N:14]([CH3:33])[N:15]=[C:16]([CH2:28][O:29][CH2:30][O:31][CH3:32])[C:17]=1[O:42][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(2,6-diethyl-4-methylphenyl)-6-methoxymethoxymethyl-5-(4-methylphenylsulfonyl)-2-methyl-3(2H)-pyridazinone (2.38 g, 4.91 mmol) and benzylalcohol (797 mg, 7.37 mmol) in dry DMF (10 ml) was added 60% sodium hydride (294 mg, 7.35 mmol) at 5° C. The reaction solution was stirred at 0° C. for 1 hour. The reaction solution was diluted with water, and extracted with tert-butyl methyl ether 2 times. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 2.12 g of 4-(2,6-diethyl-4-methylphenyl)-6-methoxymethoxymethyl-5-benzyloxy-2-methyl-3(2H)-pyridazinone (yield: 99%) as oil.

Workup

extractionextracted with tert-butyl methyl ether 2 times
washThe combined organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-12254ee38f934c2c8409028446461a3d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029295B2

Reaction notes

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