Ammonium Chloride → HCID 66960204, compound

HRID 1362682Notes

Reaction equation

HRID 1362682 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1)[CH:6]=O.[CH2:17]([O:19][C:20](=[O:40])[CH:21](P(OCC)(OCC)=O)[CH2:22][CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1)[CH3:18].O.[OH-].[Li+].[Cl-].[NH4+]>C(OCC)(=O)C.C1COCC1>[CH2:17]([O:19][C:20](=[O:40])/[C:21](=[CH:6]/[C:5]1[CH:8]=[CH:9][C:10]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)=[C:3]([O:2][CH3:1])[CH:4]=1)/[CH2:22][CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1)[CH3:18]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 14649483HCID 14649483, compoundHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 66960204HCID 66960204, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a THF (5 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (283 mg) obtained in Example 1 and 2-(diethoxyphosphoryl)-5-(tetrahydropyran-2-yloxy)valeric acid ethyl ester (480 mg), lithium hydroxide monohydrate (110 mg) was added, and the reaction solution was agitated at room temperature for 19 hours. Ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH and elution solvent: hexane:ethyl acetate=1:1→ethyl acetate), and 186 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH and elution solvent: hexane:ethyl acetate=1:1→ethyl acetate)

Sources & evidence

ORD record
ord-6e887e1b8aed45838992c6a38fc53b1f
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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