Ethyl orthoformate → 4-(2-Hydroxyethyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde
Reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[C:8]([CH3:20])=[C:9]([C:13](OC(C)(C)C)=[O:14])[NH:10][C:11]=1[CH3:12])(=O)C.C(OC(OCC)OCC)C>C(O)(C(F)(F)F)=O>[CH3:20][C:8]1[C:7]([CH2:6][CH2:5][OH:4])=[C:11]([CH3:12])[NH:10][C:9]=1[CH:13]=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
tert-Butyl 4-(2-acetoxyethyl)-3,5-dimethylpyrrole-2-carboxylate (15 g, 53 mmol) was dissolved in TFA (40 ml) and the solution was stirred at 40° C. under nitrogen for 10 min. The reaction mixture was then cooled to 0° C. and triethylorthoformate (9.6 ml, 58 mmol) was added dropwise. The mixture was allowed to warm up to 20° C. and was stirred for 1 hr before being poured into ice water. This was extracted with dichloromethane and the extracts were washed successively with 10% aqueous ammonia and water and dried over MgSO4. 4-(2-acetoxyethyl)-3,5-dimethylpyrrole-2-carboxaldehyde was purified by silica gel chromatography using (7:3) ethyl acetate:hexane. Yield 45%, m.p. 125–27° C. (water).
Workup
- temperatureThe reaction mixture was then cooled to 0° C.
- temperatureto warm up to 20° C.
- stirringwas stirred for 1 hr
- extractionThis was extracted with dichloromethane
- washthe extracts were washed successively with 10% aqueous ammonia and water
- dry with materialdried over MgSO4
- custom4-(2-acetoxyethyl)-3,5-dimethylpyrrole-2-carboxaldehyde was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-eaebc86c6ecc4838a53f00dd163dee4b
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07060822B1
Reaction notes
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