HCID 10633115, compound → HCID 22493753, compound

HRID 1643182Notes

Reaction equation

HRID 1643182 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-c63f00e5ea25485d9e4010a27ec7624c
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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