Diethyl Ether → HCID 22493753, compound

HRID 1816414Notes

Reaction equation

HRID 1816414 reaction equation
[CH2:1]([N:5]1[C:9]([CH:10]=[O:11])=[CH:8][N:7]=[C:6]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[CH2:18](OCC)C>>[CH2:1]([N:5]1[C:9]([CH:10]([OH:11])[CH3:18])=[CH:8][N:7]=[C:6]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 3283Diethyl EtherHCID 10633115HCID 10633115, compound

Product 1

HCID 22493753HCID 22493753, compound

Procedure

A solution of aldehyde 102 (230 mg) in diethyl ether (30 mL) is placed in a separatory funnel and treated with a solution of Preparation of 1-(1-Butyl)-2-phenyl-5-(1-[N-[{3,4-methylenedioxyphenylmethyl]}-N-[phenylmethyl]aminoethylimidazole) methyl lithium (1.4 M in THF, 1.5 ml). After 10 min. the solution is washed with ammonium chloride solution (1 M, 20 ml), dried (Na2SO4) and concentrated. The resulting dark oil is purified by preparative TLC (10% MeOH/CHCl3) to provide compound 107 as a colorless oil (180 mg). 1H NMR (400 MHz, CDCl3) δ 7.56 (d, J=2 Hz, 2H), 7.4 (m, 3H), 7.01 (s, 1H), 4.86 (q, J=7 Hz, 1H), 4.18 (m, 1H), 4.0 (m, 1H), 1.63 (d, J=6.6 Hz, 3H), 1.63 (m, 2H), 1.23 (m, 2H), 0.81 (t, J=7 Hz, 3H).

Workup

  1. washAfter 10 min. the solution is washed with ammonium chloride solution (1 M, 20 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe resulting dark oil is purified by preparative TLC (10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-688cc37fc07b4582bfe8180799a3d035
Source dataset
uspto-grants-2005_04
Patent number
US06884815B1

Reaction notes

Loading…