Water → HCID 18323821, compound

HRID 1872036Notes

Reaction equation

HRID 1872036 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:21][CH3:22])[C:12]1[N:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH2:19][OH:20])[N:13]=1.[H-].[Na+].I[CH3:26].O>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[CH:5]=[CH:4][C:3]=1[N:11]([CH2:21][CH3:22])[C:12]1[N:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH2:19][O:20][CH3:26])[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18323802HCID 18323802, compound

Product 1

HCID 18323821HCID 18323821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product of Example 24 and sodium hydride (1.1 eq.) in dry THF under nitrogen was added iodomethane (1.1 eq.) and after four hours the reaction was poured into H2O and extracted three times with CHCl3. The combined extracts were dried over MgSO4, filtered, and evaporated under vacuum. The material was purified by chromatography on silica gel using 10% EtOAc in hexanes to give a light yellow oil. (Rf =0.37)

Workup

  1. extractionextracted three times with CHCl3
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe material was purified by chromatography on silica gel using 10% EtOAc in hexanes
  6. customto give a light yellow oil

Sources & evidence

ORD record
ord-ef9c1ffade654a8ab75c122280fdb1a5
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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