Diethyl Ether → HCID 69662130, compound

HRID 892110Notes

Reaction equation

HRID 892110 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[C:9]1C(OC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][Mg]Br.C([O:40][CH2:41][CH3:42])C>O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[C:9]1[C:41]([OH:40])([CH3:42])[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 69662218HCID 69662218, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 69662130HCID 69662130, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 47 (100 mg, 0.218 mmol) obtained in Example 47 was dissolved in tetrahydrofuran (5 mL), to the solution was added a 3.0 mol/L solution (500 μL) of methyl magnesium bromide (1.50 mmol, 6.8 equivalents) in diethyl ether, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure and then the residue was directly purified by silica gel column chromatography (chloroform:methanol=95:5) to obtain the title compound (60 mg, 60%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was directly purified by silica gel column chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-737bd8f8d0654a00b74a21aa48c54cd1
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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