Ammonium Chloride → 858036-12-1

HRID 931164Notes

Reaction equation

HRID 931164 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[N:11]1([C:16]2([C:19](OCC)=[O:20])[CH2:18][CH2:17]2)[CH:15]=[CH:14][N:13]=[CH:12]1.[Cl-].[NH4+]>ClCCl>[N:11]1([C:16]2([CH2:19][OH:20])[CH2:18][CH2:17]2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 89853382HCID 89853382, compound

Product 1

HCID 77230224858036-12-1Yield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminum hydride (1M in tetrahydrofuran, 8 mL, 8 mmol) was added dropwise to a solution of ethyl 1-(1H-imidazol-1-yl)cyclopropanecarboxylate (0.3 g, 1.6 mmol) in anhydrous dichloromethane (20 mL) at −78° C. The reaction mixture was warmed to room temperature and stirred at that temperature for 5 h. A saturated aqueous solution of ammonium chloride was added and the mixture was stirred for 30 min. The resulting solids were filtered through a pad of Celite and the filtrate was dried over sodium sulfate. The organics were concentrated under reduced pressure and the crude material was purified via column chromatography (100-200 mesh silica gel, 0-6% methanol in dichlormethane) to afford (1-(1H-imidazol-1-yl)cyclopropyl)methanol 0.15 g). MS (ES+APCI) (M+H) 139.1.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. filtrationThe resulting solids were filtered through a pad of Celite
  3. dry with materialthe filtrate was dried over sodium sulfate
  4. concentrationThe organics were concentrated under reduced pressure
  5. customthe crude material was purified via column chromatography (100-200 mesh silica gel, 0-6% methanol in dichlormethane)

Sources & evidence

ORD record
ord-91a3f91383c04df8bc2137ee7850c709
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

Loading…