Triethylamine → Acetaldehyde, 2-(2-phenylethoxy)-

HRID 863846Notes

Reaction equation

HRID 863846 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC>CS(C)=O.C(Cl)Cl.CCOCC>[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 132089292-(2-Phenylethoxy)ethanol

Product 1

HCID 162493Acetaldehyde, 2-(2-phenylethoxy)-

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Procedure

To 2-(2-phenylethoxy)-1-ethanol (0.25 g; 1.5 mmol) [J. Med. Chem., 1570 (1983)] dissolved in DMSO/CH2Cl2 (4 ml/2 ml) is added Et3N (1 ml; 7 mmol) followed by sulfur trioxide pyridine complex (1.2 g; 7.5 mmol). After 10 minutes, the reaction mixture is then diluted with Et2O and washed with brine, 1N HCl, NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using CH2Cl2 to obtain 2-phenylethoxyacetaldehyde which is used directly in Step B.

Workup

  1. washwashed with brine, 1N HCl, NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-275b6da7e74f405585cb46aea7d935ec
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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