HCID 10633115, compound → HCID 22493753, compound

HRID 457347Notes

Reaction equation

HRID 457347 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].[CH3:18][Li]>C(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

4

Reactant 2

HCID 10633115HCID 10633115, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22493753HCID 22493753, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 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. 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. washthe 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-a75f82cde1aa4851aa0c18a06e9f3c1c
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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