Triethylamine → (+-)-Trans-2-formyl-cyclopropanecarboxylic acid ethyl ester

HRID 20452

Reaction equation

HRID 20452 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[CH2:9][OH:10])=[O:5])[CH3:2].C(N(CC)CC)C.N1C=CC=CC=1.S(=O)(=O)=O>CS(C)=O.C(OCC)C>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[CH:9]=[O:10])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 29920784Ethyl (1R,2R)-2-(hydroxymethyl)cyclopropanecarboxylate

Product 1

HCID 7271792(+-)-Trans-2-formyl-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

Cool a solution of (+/−)-trans-2-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (0.22 g, 1.53 mmol) in 1.5 mL DMSO to 0° C. Add to the frozen solution triethyl-amine (0.85 mL, 0.62 mmol) followed by sulfur trioxide pyridine (0.49 g, 3.05 mmol). Warm reaction mixture to 12° C. over 3.5 hours, dilute with diethyl ether (80 mL), and wash with 5% aqueous citric acid (3×20 mL) followed by saturated aqueous sodium chloride (1×20 mL). Dry over magnesium sulfate and concentrate under reduced pressure to provide the desired compound.

Workup

  1. temperatureWarm
  2. customreaction mixture to 12° C. over 3.5 hours
  3. washwash with 5% aqueous citric acid (3×20 mL)
  4. dry with materialDry over magnesium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-37767759e28946f6af4b9007458d87cf
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

Loading…