Sulfuric Acid → 2-(4-Chloro-3-methoxy-2-pyridyl)-2-cyclopropylethanal
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:9][O:10]C)[C:3]=1[O:15][CH3:16].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH:12]2[CH2:13][CH2:14]2)[CH:9]=[O:10])[C:3]=1[O:15][CH3:16]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
4-chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine (259 mg, 1.1 mmol) was dissolved in THF (10 ml) and cooled to 0° C. 4M sulfuric acid (2.7 ml, 10 mmol) was added and the reaction was performed at reduced pressure while heating at 50° C. for 2.5 h. The mixture was diluted in ice water (10 mL) and sodium bicarbonate added until neutralized. The mixture was washed with DCM (3×10 mL) and the organic phase dried, filtered and evaporated to dryness to obtain 2-(4-chloro-3-methoxy-pyridin-2-yl)-2-cyclopropyl-acetaldehyde as a yellow oil (233 mg) to be used without further purification.
Workup
- temperaturewhile heating at 50° C. for 2.5 h
- washThe mixture was washed with DCM (3×10 mL)
- customthe organic phase dried
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-a0c0ceebbb554eb49d2978c3bd32ae88
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09403818B2
Reaction notes
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