Acetone → HCID 11615861, compound

HRID 2245807Notes

Reaction equation

HRID 2245807 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=2)[CH:11]=1.CC(C)=O>O1CCCC1.[Cl-].[Na+].O>[CH3:24][N:23]([CH3:25])[C:20]1[CH:19]=[CH:18][C:17]([S:16][C:12]2[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][CH:13]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 11673663HCID 11673663, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11615861HCID 11615861, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of lithium aluminium hydride (61 mg, 1.1 mmol) in dry tetrahydrofuran (2 mL) at 0° C., under an argon atmosphere, was added a solution of 3-(4-dimethylamino-phenylsulfanyl)-benzoic acid methyl ester (287 mg, 1.0 mmol) in dry tetrahydrofuran (4 mL) in a dropwise manner. The mixture was stirred at room temperature for 1 hour and then cooled to 0° C. Acetone (2 mL) was added dropwise followed by brine (8 mL) to give a slurry that was filtered through a pad of celite, which was washed with ethyl acetate (3×10 mL). The organic layer was washed with brine (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give the title compound (255 mg, 98%) as a colourless oil.

Workup

  1. temperaturecooled to 0° C
  2. customto give a slurry that
  3. filtrationwas filtered through a pad of celite, which
  4. washwas washed with ethyl acetate (3×10 mL)
  5. washThe organic layer was washed with brine (25 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27e5fb9ad9574d0794efed8739952984
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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