Water → HCID 18786362, compound

HRID 1418502Notes

Reaction equation

HRID 1418502 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26](OC)=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>Cl>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([CH2:26][OH:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18786327HCID 18786327, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18786362HCID 18786362, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of methyl 4-[3-[4-(2-methylimidazol-1-yl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate(359 mg,0.9 mmol) was added LAH (80 mg, 2.0 mmol) at 0° C. After completion of addition, the mixture was allowed to warm to room temperature. To the reaction mixture was carefully added water (1 ml), and the resulting solids were dissolved in 1N aqueous HCl and the aqueous solution was basified with 1N aqueous NaOH. The aqueous mixture was extracted with ethyl acetate (30 ml×3), and the combined extracts were washed with water (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography {LiChroprep NH2 (Merck), 20 g; eluted with ethyl acetate} to afford 231 mg (69%) of the desired compound as white solids.

Workup

  1. additionAfter completion of addition
  2. extractionThe aqueous mixture was extracted with ethyl acetate (30 ml×3)
  3. washthe combined extracts were washed with water (50 ml) and brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography {LiChroprep NH2 (Merck), 20 g
  7. washeluted with ethyl acetate}

Sources & evidence

ORD record
ord-199647accb9e4ff78ce7c5e0c9bd7163
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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