Hydrochloric Acid → 3-Methoxythiophene-2-carbaldehyde

3-Methoxy-2-thiophenecarboxadlehyde was prepared by adding n-butyllithium (10.56 mmol, 2.5M solution in hexane)(Aldrich), without cooling, to a solution of 3-methoxythiophene (1 g,8.8 mmol) (Aldrich) in dry diethyl ether (5 mL) over a period of 5 min. The mixture was gently heated at reflux for 2 h at which time the organolithium compound was transferred, via cannula, to a solution of DMF (23 mmol) in diethyl ether (5 mL) which was cooled in an ice bath. The reaction was stirred at room temperature for 14 h, at which time 1N HCl (10 mL) was added and the layers were separated. The aqueous layer was extracted with diethyl ether (3×25 mL), and the combined organic extracts were dried over magnesium sulfate, and concentrated to yield 3-methoxy-2-thiophenecarboxaldehyde as a pale, yellow solid. The 3-methoxy-2-thiophenecarboxaldehyde was then added to ethynylmagnesium chloride (Aldrich) according to Method A above to yield 3-hydroxy-3-(3-methoxy-2-thiophenyl)-1-propyne. (Yield 151 mg, 0.9 mmol).

1. custom3-Methoxy-2-thiophenecarboxadlehyde was prepared
2. temperatureThe mixture was gently heated
3. temperaturewas cooled in an ice bath
4. additionwas added
5. customthe layers were separated
6. extractionThe aqueous layer was extracted with diethyl ether (3×25 mL)
7. dry with materialthe combined organic extracts were dried over magnesium sulfate
8. concentrationconcentrated

ORD-Eintrag

ord-80e3866d1927492dbb1ee79bb90fa322

Quelldatensatz

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06313310B1