Hydrochloric Acid → HCID 86591572, compound

HRID 1294228Notes

Reaction equation

HRID 1294228 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23](OC)=[O:24].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[CH:23]=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 68883448HCID 68883448, compound

Product 1

HCID 86591572HCID 86591572, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzoate (2.20 g) and tetrahydrofuran (80 mL) was added lithium aluminum hydride (0.19 g) under ice-cooling, and the mixture was stirred for 2 hrs. The reaction mixture was poured into iced water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The obtained oil was dissolved in toluene (80 mL). Manganese dioxide (6.0 g) was added to the mixture and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was filtrated and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzaldehyde as an oil (1.55 g, yield 76%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe obtained oil was dissolved in toluene (80 mL)
  7. additionManganese dioxide (6.0 g) was added to the mixture
  8. stirringthe mixture was stirred at room temperature for 2 hrs
  9. filtrationThe reaction mixture was filtrated
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-73b08f3946904344a9e78793b307100a
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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