Methyl iodide → HCID 59773514, compound

HRID 2220746Notes

Reaction equation

HRID 2220746 reaction equation
[N:1]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li][CH2:14]CCC.CI.[NH4+].[Cl-]>C1COCC1>[CH3:14][N:6]1[C:7](=[O:12])[CH2:8][CH2:9][CH2:10][C:11]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 1228303261479-36-5HCID 178418339Butyllithium

Product 1

HCID 59773514HCID 59773514, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.0 eq of 96 in 30 mL of dry THF was cooled to −78° C. While stirring, 1.1 eq of n-BuLi (2.5 M in hexanes) was added dropwise. The reaction solution was warmed to 0° C. and stirred for 1 hr. The solution was then cooled to −78° C. and 1.2 eq of methyl iodide was slowly added. The mixture was stirred, as the solution warmed to rt. After 17 hrs, 50 mL of saturated NH4Cl was added and extracted with EtOAc (3×50 mL). The combined organic extracts were dried over MgSO4 and vacuum filtered. The filtrate was rotary evaporated and dried under vacuum to afford a dark orange colored solid as 97.

Workup

  1. stirringstirred for 1 hr
  2. temperatureThe solution was then cooled to −78° C.
  3. stirringThe mixture was stirred, as the solution
  4. temperaturewarmed to rt
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4 and vacuum
  7. filtrationfiltered
  8. customThe filtrate was rotary evaporated
  9. customdried under vacuum
  10. customto afford a dark orange colored solid as 97

Sources & evidence

ORD record
ord-ed2fb03b0ca143c6b1f69e97269dd8fb
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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