Diethyl Ether → HCID 20714165, compound

HRID 1725967Notes

Reaction equation

HRID 1725967 reaction equation
[CH3:1][C:2]([CH3:13])([C:5](=O)[N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:3]#[N:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+].C(OCC)C>C1COCC1>[CH3:1][C:2]([CH3:13])([CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][NH2:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 60778595HCID 60778595, compound

Product 1

HCID 20714165HCID 20714165, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 393A (0.9 g, 5 mmol) in 10 mL of THF was treated with a 1M solution of LAH in THF (10 mL, 10 mmol), stirred at room temperature for 6 hours, cooled to 0° C., and treated with 10 mL of saturated ammonium chloride and 30 mL of diethyl ether. The organic layer was washed with saturated ammonium chloride solution (3×), dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 171 (M+H)+.

Workup

  1. temperaturecooled to 0° C.
  2. washThe organic layer was washed with saturated ammonium chloride solution (3×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-addb2e06ea884d0cb4bfbec687ecf521
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

Loading…