Water → HCID 18707226, compound

HRID 1421996Notes

Reaction equation

HRID 1421996 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[C:26]([C:38](OC)=[O:39])[CH:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[C:26]([CH2:38][OH:39])[CH:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 18707383HCID 18707383, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18707226HCID 18707226, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

548 mg of lithium aluminum hydride was added to a solution of 5.43 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-tert-butyldimethylsilyloxyphenyl)thiazole in 100 ml of tetrahydrofuran, with ice-cooling. The mixture was stirred at the same temperature for 7 hours. To the reaction mixture were added 1.1 ml of water and 3 g of sodium sulfate. The resulting mixture was filtered through Celite. The filtrate was subjected to distillation to remove the solvent. To the residue were added 200 ml of ethyl acetate and 50 ml of water. The mixture was neutralized with 5 N hydrochloric acid. The insoluble was removed by filtration. The filtrate was subjected to phase separation. The organic layer was washed with 50 ml of water, dried over anhydrous magnesium sulfate and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=10/1 by v/v) and recrystallized from ethyl acetate-n-hexane to obtain 1.23 g of 2-(3,4-diethoxyphenyl)-4-(3-hydroxymethyl-4-tert-butyldimethylsilyloxyphenyl)thiazole.

Workup

  1. temperaturecooling
  2. filtrationThe resulting mixture was filtered through Celite
  3. distillationThe filtrate was subjected to distillation
  4. customto remove the solvent
  5. additionTo the residue were added 200 ml of ethyl acetate and 50 ml of water
  6. customThe insoluble was removed by filtration
  7. customThe filtrate was subjected to phase separation
  8. washThe organic layer was washed with 50 ml of water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationsubjected to distillation
  11. customto remove the solvent
  12. customThe residue was purified by silica gel column chromatography (eluent; n-hexane/ethyl acetate=10/1 by v/v)
  13. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-27db58ce8d534b4db8c2e55576134283
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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