Water → 3-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

HRID 240299Notes

Reaction equation

HRID 240299 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][C:27](OCC)=[O:28])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27][OH:28])[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19930435Ethyl 3-(1-trityl-1H-imidazol-4-yl)propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

Ethyl 3-(1-trityl-4-imidazolyl)propionate (93.0 g, 223 mmol) in tetrahydrofuran/diethyl ether (1:1, 100 mL) was added dropwise to a suspension of lithium aluminium hydride (17.0 g, 446 mmol) during 1 hr. The mixture was refluxed for 3 hrs, then treated with water (100 mL), 20% sodium hydroxide (100 mL) and water (100 mL) under cooling with ice/water, filtered and the solid washed with tetrahydrofuran. The organic phase was dried over anhydrous potassium carbonate, filtered and evaporated to give 3-(1-trityl-4-imidazolyl)propanol as white solid.

Workup

  1. temperatureThe mixture was refluxed for 3 hrs
  2. filtrationfiltered
  3. washthe solid washed with tetrahydrofuran
  4. dry with materialThe organic phase was dried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-be029ac2e65a4e1ab718b4b9f1c974a6
Source dataset
uspto-grants-2014_02
Patent number
US08648041B2

Reaction notes

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