Diethyl Ether → HCID 22400605, compound

HRID 260810Notes

Reaction equation

HRID 260810 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.C[C:13]([NH2:17])(C)CO.S(Cl)(Cl)=O.CCO[CH2:25][CH3:26].[CH2:27](Cl)Cl>>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([C:1]2[O:10][C:25]([CH3:26])([CH3:27])[CH2:13][N:17]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6344Dichloromethane2×HCID 118072-Amino-2-methyl-1-propanolHCID 24386Thionyl ChlorideHCID 74374m-Anisoyl chloride

Product 1

HCID 22400605HCID 22400605, compound

Procedure

To a 500 mL, 3-neck, round-bottom flask equipped with thermometer, condenser, addition funnel, and magnetic stirring, was added 43.2 g (253 mmoles) of m-anisoyl chloride in 500 mL of methylene chloride. The solution was cooled on ice and 2-methyl-2-aminopropanol (56.4 g, 60.4 mL, 633 mmoles) dissolved in 50 mL of methylene chloride was added slowly with stirring. The mixture was allowed to warm to room temperature and was stirred overnight. The solution was filtered from solids, and solvent was removed in vacuo. With ice cooling, thionyl chloride (90.8 g, 55.7 mL, 763 mmoles) was added to the remaining oil. The mixture was stirred for 1 hour at room temperature, and poured into 1 L of ether. The ether was decanted, and the remaining oil was carefully poured into 100 mL of 20% sodium hydroxide with ice cooling. After extraction several times with ether, the organic phases were combined, dried over magnesium sulfate, and solvent was removed in vacuo to yield a viscous yellow oil. The crude material was purified by column chromatography (1:1 ether:hexanes), or by distillation (5 mm Hg, b.p.=150° C.), to yield a low-melting solid.

Workup

  1. customTo a 500 mL, 3-neck, round-bottom flask equipped with thermometer, condenser, addition funnel, and magnetic stirring
  2. additionwas added slowly
  3. stirringwas stirred overnight
  4. filtrationThe solution was filtered from solids, and solvent
  5. customwas removed in vacuo
  6. stirringThe mixture was stirred for 1 hour at room temperature
  7. customThe ether was decanted
  8. additionthe remaining oil was carefully poured into 100 mL of 20% sodium hydroxide with ice cooling
  9. extractionAfter extraction several times with ether
  10. dry with materialdried over magnesium sulfate, and solvent
  11. customwas removed in vacuo
  12. customto yield a viscous yellow oil
  13. customThe crude material was purified by column chromatography (1:1 ether:hexanes)
  14. distillationby distillation (5 mm Hg, b.p.=150° C.)
  15. customto yield a low-melting solid

Sources & evidence

ORD record
ord-c6d309e6dc7e4b8595cb2b52ec1d69d2
Source dataset
uspto-grants-1996_06
Patent number
US05530028

Reaction notes

Loading…