Water → HCID 18786390, compound

HRID 1108112Notes

Reaction equation

HRID 1108112 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([CH:26]=[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

Participants

6

Reactant 4

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

Product 1

HCID 18786390HCID 18786390, 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 1 N aqueous HCl and the aqueous solution was basified with 1 N 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-59bd4230846a4d3c90430ec79124ddf7
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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