Sodium Hydroxide → HCID 10522854, compound

HRID 1532729Notes

Reaction equation

HRID 1532729 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1.[H][H].[CH3:18][C:19]1[O:23][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:21][C:20]=1[C:30]1C=C(S(OCC)(=O)=O)C=C[C:31]=1C.[OH-].[Na+]>CCCCCC.CN(C)C=O.C(OCC)(=O)C>[CH3:18][C:19]1[O:23][C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:21][C:20]=1[CH2:30][CH2:31][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 22013884HCID 22013884, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10522854HCID 10522854, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil, 2.11 g, 88.1 mmol) was washed twice with n-hexane (10 ml) under a nitrogen atmosphere, suspended in N,N-dimethylformamide (50 ml) and ice-cooled. To this solution was added methyl 3-(p-hydroxyphenyl)propionate (15.9 g, 88.1 mol) over 15 min. After 10 min when hydrogen bubbling finished, a solution of ethyl 2-(5-methyl-2-phenyl-4-oxazolyl)-p-toluenesulfonate (20.0 g, 56.0 mmol) in N,N-dimethylformamide (50 ml) was added. The mixture was stirred at room temperature for 5 hr, and ethyl aceate (500 ml) and 1N aqueous sodium hydroxide solution (200 ml) were added for partition. The obtained organic layer was washed with 1N hydrochloric acid (100 ml), saturated aqueous sodium hydrogencarbonate solution (100 ml) and saturated brine (100 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=85:15) to give the title compound (14.0 g, yield 68%) as a white solid.

Workup

  1. temperatureice-cooled
  2. customfor partition
  3. washThe obtained organic layer was washed with 1N hydrochloric acid (100 ml), saturated aqueous sodium hydrogencarbonate solution (100 ml) and saturated brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-47b79440835e422b824e2b02d61c543f
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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