Morpholine → HCID 14568660, compound

HRID 34118

Reaction equation

HRID 34118 reaction equation
[C:1]([O:4][CH2:5][C:6]1[O:10][C:9]([CH:11]=O)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[N:13]1([CH2:11][C:9]2[O:10][C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])=[CH:7][CH:8]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 663495-Acetoxymethyl-2-furaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 14568660HCID 14568660, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, to a solution of 2.0 g of 5-acetoxymethyl-2-furanaldehyde and 1.1 mL of morpholine in 35 mL of 1,2-dichloroethane was added 4.0 g of sodium triacetoxy borohydride at room temperature, and stirred at this temperature for 3 hours. The reaction solution was diluted with dichloromethane, washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified and separated by silica gel column chromatography, to afford 2.3 g of the title compound as a colorless oil.

Workup

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified
  5. customseparated by silica gel column chromatography

Sources & evidence

ORD record
ord-c408746cbab8470790f98487d756d10d
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Linked notes

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