Dimethyl Sulfoxide → 4-Tert-butylmorpholine-2-carbaldehyde

HRID 603257Notes

Reaction equation

HRID 603257 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:15]1[CH2:20][CH2:19][O:18][CH:17]([CH2:21][OH:22])[CH2:16]1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([N:15]1[CH2:20][CH2:19][O:18][CH:17]([CH:21]=[O:22])[CH2:16]1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58902595(4-Tert-butylmorpholin-2-yl)methanol

Product 1

HCID 576569134-Tert-butylmorpholine-2-carbaldehydeYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalyl chloride (0.097 mL) in dichloromethane (10 mL) was cooled to −78° C. under argon. A solution of dimethylsulfoxide (0.201 mL) in dichloromethane (5 mL) was added dropwise and the mixture was stirred for 5 minutes. A solution of (4-tert-butylmorpholin-2-yl)methanol (175 mg) in dichloromethane (3 mL) was added and the mixture was stirred for 15 minutes. Triethylamine (0.845 mL) was added and the mixture was warmed to room temperature. The reaction was quenched with water and partitioned between water and dichloromethane. The organic layer was dried (Na2SO4), filtered and concentrated to give an orange oil (165 mg). This material was used immediately in the next stage without further purification or analysis.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. customThe reaction was quenched with water
  3. custompartitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71b29e56fe3545699ce1fdbbcf8b89f7
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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