Dimethyl Sulfoxide → (Methyl(trityl)amino)acetaldehyde

HRID 23719Notes

Reaction equation

HRID 23719 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.N#N.[CH3:13][N:14]([C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:15][CH2:16][OH:17].C(N(CC)CC)C>C(Cl)Cl>[CH3:13][N:14]([CH2:15][CH:16]=[O:17])[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 947NitrogenHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5080555566949-46-0

Product 1

HCID 85849001(Methyl(trityl)amino)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of DMSO (1.47 mL, 20.8 mmol) in 60 mL of CH2Cl2 was cooled to −78° C. and treated with oxalyl chloride dropwise under N2 atmosphere for 10 min. The resulting mixture was treated with a solution of 2-[methyl(trityl)amino]ethanol (3.0 g, 9.45 mmol) in 10 mL of CH2Cl2 dropwise and stirred for additional 15 min. Triethylamine (6.6 mL, 47.3 mmole) was added to the mixture and warmed up to room temperature. The reaction was quenched by adding water and diluted with 100 mL of CH2Cl2. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with ether to give the product as white solid.

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. additiondiluted with 100 mL of CH2Cl2
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-56ccc7f70d6443868d0e1b72742fc30d
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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