Ammonium Chloride → HCID 178515241, compound

HRID 926278Notes

Reaction equation

HRID 926278 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2([OH:17])[CH2:16][O:15][CH2:14]2)[N:10]=[CH:9]1)C1C=CC=CC=1.C(N1C=C(I)N=C1)C1C=CC=CC=1.CC[Mg+].[Br-].[NH4+].[Cl-]>C(Cl)Cl>[NH:8]1[CH:12]=[C:11]([C:13]2([OH:17])[CH2:16][O:15][CH2:14]2)[N:10]=[CH:9]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 113919601-Benzyl-4-iodoimidazoleHCID 86711353HCID 86711353, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 178515241HCID 178515241, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1-benzyl-1H-imidazol-4-yl)oxetan-3-ol. A solution of 1-benzyl-4-iodo-1H-imidazole (6.0 g, 21.12 mmol) in DCM (80 mL) was treated with EtMgBr (3M in ether, 7.74 mL, 23.23 mmol) at rt and the mixture was stirred at RT overnight. The mixture was then poured onto saturated aqueous NH4Cl solution and extracted with DCM. The combined org. layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent: 1% MeOH in DCM for 3 min, then from 1% MeOH in DCM to 5% MeOH in DCM in 25 min, followed by 5% MeOH in DCM for 6 min). The residue was crystallized from EtOAc to yield the title compound as white crystals (2.35 g). UPLC-MS: MS 231.1 (M+H+); UPLC rt 0.43 min.

Workup

  1. extractionextracted with DCM
  2. dry with materiallayers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash-column chromatography over silicagel (Biotage Isolera Four, eluent
  6. wait1% MeOH in DCM for 3 min
  7. waitfrom 1% MeOH in DCM to 5% MeOH in DCM in 25 min
  8. waitfollowed by 5% MeOH in DCM for 6 min
  9. customThe residue was crystallized from EtOAc

Sources & evidence

ORD record
ord-db26512808f34691a973cc40f6723329
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

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