methyl 1-trityl-1H-imidazole-4-carboxylate → 1-(1-trityl-1H-imidazol-4-yl)cyclopropanol

HRID 532902Notes

Reaction equation

HRID 532902 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([C:25]([O:27]C)=O)[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.[CH3:29][CH2:30][Mg+].[Br-]>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[C:1]([N:20]1[CH:24]=[C:23]([C:25]2([OH:27])[CH2:30][CH2:29]2)[N:22]=[CH:21]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 10429115methyl 1-trityl-1H-imidazole-4-carboxylateHCID 178461630HCID 178461630, compound

Product 1

HCID 867113491-(1-trityl-1H-imidazol-4-yl)cyclopropanolYield 4%

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 1-trityl-1H-imidazole-4-carboxylate (11.0 g, 29.9 mmol) and Ti(OiPr)4 (12.37 mL, 41.8 mmol) in THF (3 mL) was treated dropwise with a 1M solution of EtMgBr (76 mL, 76 mmol) to maintain the temperature below 35° C. The mixture was then stirred at RT for 4 h, and then poured onto H2O. The precipitate was filtered off, and the filtrate was extracted with AcOEt. The combined org. layers were dried over Na2O4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, AcOEt/heptane 30:70 to 100:0) gave the title compound (440 mg). UPLC-MS: MS 367.3 (M+H+); UPLC rt 1.01 min.

Workup

  1. temperatureto maintain the temperature below 35° C
  2. additionpoured onto H2O
  3. filtrationThe precipitate was filtered off
  4. extractionthe filtrate was extracted with AcOEt
  5. customlayers were dried over Na2O4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography (SiO2, AcOEt/heptane 30:70 to 100:0)

Sources & evidence

ORD record
ord-90554e6120374b9e97f750425578614b
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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