Hydrochloric Acid → HCID 58679072, compound

HRID 1442536Notes

Reaction equation

HRID 1442536 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:9]([CH:14]=1)[C:10](OC)=[O:11])(=[O:4])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:9]([CH:14]=1)[CH2:10][OH:11])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 59165549HCID 59165549, compound

Product 1

HCID 58679072HCID 58679072, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-methanesulfonyl-2-(morpholin-4-yl)benzoate obtained in Step 3 in tetrahydrofuran (300 ml) was added lithium aluminum hydride (3.6 g, 94 mmol) by small portions under ice-cooling. After stirring under ice-cooling for 1 hr, 1N hydrochloric acid (200 ml) was slowly added and the mixture was stirred at room temperature for 1 hr. After extraction with ethyl acetate (500 ml), the organic layer was washed with saturated brine (200 ml×3), and dried over magnesium sulfate. After filtration and concentration, the resulting solid was collected by filtration. The solid was washed with a mixed solvent (100 ml) of hexane-ethyl acetate (4:1) to give 5-methanesulfonyl-2-(morpholin-4-yl)benzyl alcohol (8.6 g, yield 34%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. extractionAfter extraction with ethyl acetate (500 ml)
  5. washthe organic layer was washed with saturated brine (200 ml×3)
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration and concentration
  8. filtrationthe resulting solid was collected by filtration
  9. washThe solid was washed with a mixed solvent (100 ml) of hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-69dbe3a1b645491c88b2f6f6c5e3a3ce
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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