Potassium Sodium Tartrate → 1-(1-Trityl-1H-imidazol-4-yl)propane-1,3-diol

HRID 724206Notes

Reaction equation

HRID 724206 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH:8]([C:15]1[N:16]=[CH:17][N:18]([C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=1)[CH2:9][C:10](OCC)=[O:11].O.C1COCC1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[C:20]([N:18]1[CH:19]=[C:15]([CH:8]([OH:7])[CH2:9][CH2:10][OH:11])[N:16]=[CH:17]1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 21879633Ethyl 3-hydroxy-3-(1-trityl-1h-imidazol-4-yl)propanoateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 218796071-(1-Trityl-1H-imidazol-4-yl)propane-1,3-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (8.78 g) was suspended in dry THF (500 ml) under an argon atmosphere, and ethyl 3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)propanoate (76 g)/dry THF (350 ml) solution was added at the same temperature with stirring under ice-cooling (ice-salt). The mixture was allowed to assume room temperature and stood with stirring for 2 h. The mixture was ice-cooled again and water/THF (1/6; 58.4 ml) was added to stop the reaction. An aqueous Rochelle salt solution (240 g/1.5 L) was added and the mixture was stood with stirring for 18 h. The organic layer was separated, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was recrystallized from ethyl acetate-ether to give the title compound (58.8 g) as a colorless crystalline powder.

Workup

  1. customto assume room temperature
  2. stirringwith stirring for 2 h
  3. temperaturecooled again
  4. customthe reaction
  5. stirringwith stirring for 18 h
  6. customThe organic layer was separated
  7. washwashed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated
  10. customthe residue was recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-77444139b60d4a79b2d771328a5c9f12
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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